Abstract
Isocyanide-based multicomponent reactions are among the most powerful synthetic tools available. Particularly, the isocyanide-based Ugi reaction can allow rapid preparation of \(\alpha \)-aminoacyl amide derivatives and polyazaheterocycles with extensive pharmaceutical applications. Moreover, bridged polyazaheterocycles, including one or more quaternary carbon centers, can be constructed via the Ugi cascade reaction in a few steps. This review will emphasize synthesis and bioactivities of bridged compounds with quaternary centers constructed through Ugi cascade reactions.
Similar content being viewed by others
References
Ayaz M, De Moliner F, Dietrich J, Hulme C (2013) Evolution of isocyanide chemistry. In: Nenajdenko V (ed) Wiley, Weinheim, pp 335–384
Xu H, Jia ZH, Xu K, Zhou H, Shen M (2015) One-pot protocol to functionalized benzopyrrolizidine catalyzed successively by \({\text{ Rh }}_{2}{\text{(OAc) }}_{4}\) and \({\text{ Cu(OTf) }}_{2}\): a transition metal-lewis acid catalysis relay. Org Lett 17:66–69. https://doi.org/10.1021/ol503247t
Laborda P, Sayago F, Cativiela C, Parella T, Joglar J, Clapes P (2014) Aldolase-catalyzed synthesis of conformationally constrained iminocyclitols: preparation of polyhydroxylated benzopyrrolizidines and cyclohexapyrrolizidines. Org Lett 16:1422–1425. https://doi.org/10.1021/ol5002158
Brucelle F, Renaud P (2012) Synthesis of indolines, indoles, and benzopyrrolizidinones from simple aryl azides. Org Lett 14:3048–3051. https://doi.org/10.1021/ol301120w
Dömling A, Ugi I (2000) Multicomponent reactions with isocyanides. Angew Chem Int Ed 39:3168–3210. https://doi.org/10.1002/1521-3773(20000915)
Armstrong RM, Combs AP, Tempest PA, Brown SD, Keating TA (1996) Multiple-component condensation strategies for combinatorial library synthesis. Acc Chem Res 29:123–131. https://doi.org/10.1021/ar9502083
Sunderhaus JD, Martin SF (2009) Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds. Chem Eur J 15:1300–1308. https://doi.org/10.1002/chem.200802140
Sunderhaus JD, Dockendorff C, Martin SF (2007) Applications of multicomponent reactions for the synthesis of diverse heterocyclic scaffolds. Org Lett 9:4223–4226. https://doi.org/10.1021/ol7018357
Ilyn AP, Trifilenkov AS, Kuzovkova JA, Kutepov SA, Nikitin AV, Ivachtchenko AV (2005) New four-component Ugi-type reaction. Synthesis of heterocyclic structures containing a pyrrolo[1,2-a][1,4]diazepine fragment. J Org Chem 70:1478–1481. https://doi.org/10.1021/jo048204b
Cano-Herrera MA, Miranda LD (2011) Expedient entry to the piperazinohydroisoquinoline ring system using a sequential Ugi/Pictet-Spengler/reductive methylation reaction protocol. Chem Commun 47:10770–10772. https://doi.org/10.1039/C1CC10759C
Liu X, Ma X, Huang Y, Gu Z (2013) Pd-catalyzed heck-type cascade reactions with N-tosyl hydrazones: an efficient way to alkenes via in situ generated alkylpalladium. Org Lett 15:4814–4817. https://doi.org/10.1021/ol402210a
Miranda LD, Hernández-Vázquez E (2015) Multicomponent/palladium-catalyzed cascade entry to benzopyrrolizidine derivatives: synthesis and antioxidant evaluation. J Org Chem 80:10611–10623. https://doi.org/10.1021/acs.joc.5b01742
Iwata A, Inuki S, Oishi S, Fujii N, Ohno H (2014) Synthesis of fused tetracyclic spiroindoles via palladium-catalysed cascade cyclisation. Chem Commun 50:298–300. https://doi.org/10.1039/C3CC46511J
Kim KH, Kim SH, Lee HJ, Kim JM (2013) Palladium-catalyzed domino cyclization (5-exo/3-exo), ring-expansion by palladium rearrangement, and aromatization: an expedient synthesis of 4-arylnicotinates from Morita–Baylis–Hillman adducts. Adv Synth Catal 355:1977–1983. https://doi.org/10.1002/adsc.201300211
Montgomery TD, Nibbs AE, Zhu Y, Rawal VH (2014) Rapid access to spirocyclized indolenines via palladium-catalyzed cascade reactions of tryptamine derivatives and propargyl carbonate. Org Lett 16:3480–3483. https://doi.org/10.1021/ol501409a
Montgomery TD, Zhu Y, Kagawa N, Rawal VH (2013) Palladium-catalyzed decarboxylative allylation and benzylation of N-alloc and N-Cbz indoles. Org Lett 15:1140–1143. https://doi.org/10.1021/ol400334u
Perez-Labrada K, Flórez-López E, Paz-Morales E, Mirandá LD, Rivera DG (2011) A two-step practical synthesis of dehydroalanine derivatives. Tetrahedron Lett 52:1635–1638. https://doi.org/10.1016/j.tetlet.2011.01.122
García-González MC, Hernández-Vázquez E, Gordillo-Cruz R, Miranda LD (2015) Ugi-derived dehydroalanines as a pivotal template in the diversity oriented synthesis of aza-polyheterocycles. Chem Commun 51:11669–11672. https://doi.org/10.1039/C5CC02927A
Cuny G, Bois-Choussy M, Zhu J (2004) Palladium- and copper-catalyzed synthesis of medium- and large-sized ring-fused dihydroazaphenanthrenes and 1,4-benzodiazepine-2,5-diones. Control of reaction pathway by metal-switching. J Am Chem Soc 126:14475–14484. https://doi.org/10.1021/ja047472o
Salcedo A, Neuville L, Rondot C, Retailleau P, Zhu J (2008) Palladium-catalyzed domino intramolecular N-arylation/intermolecular C–C bond formation for the synthesis of functionalized benzodiazepinediones. Org Lett 10:857–860. https://doi.org/10.1021/ol7029799
Bonnaterre F, Bois-Choussy M, Zhu J (2008) Synthesis of dihydrophenanthridines by a sequence of Ugi-4CR and palladium-catalyzed intramolecular C–H functionalization. Beilstein J Org Chem 4:10–13. https://doi.org/10.3762/bjoc.4.10
Erb W, Neuville L, Zhu J (2009) Ugi-post functionalization, from a single set of Ugi-adducts to two distinct heterocycles by microwave-assisted palladium-catalyzed cyclizations: tuning the reaction pathways by ligand switch. J Org Chem 74:3109–3115. https://doi.org/10.1021/jo900210x
Welsch SJ, Kalinski C, Umkerhke M, Ross G, Kolb J, Burdack C, Wessjohann LA (2012) Palladium and copper catalyzed cyclizations of hydrazine derived Ugi products: facile synthesis of substituted indazolones and hydroxytriazafluorendiones. Tetrahedron Lett 53:2298–2301. https://doi.org/10.1016/j.tetlet.2012.02.095
Welsch SJ, Kalinski C, Umkerhke M, Ross G, Kolb J, Burdack C, Wessjohann LA (2011) \(\text{ Pd }^{II/IV}\) catalyzed oxidative cyclization of 1,6-enynes derived by Ugi-4-component reaction. Tetrahedron Lett 52:6295–6297. https://doi.org/10.1016/j.tetlet.2011.09.094
Perez-Labrada K, Florez-Lopez E, Paz-Morales E, Miranda LD, Rivera DG (2011) A two-step practical synthesis of dehydroalanine derivatives. Tetrahedron Lett 52:1635–1638. https://doi.org/10.1016/j.tetlet.2011.01.122
Selvakumar J, Ramanathan CR (2011) Brønsted acid assisted activation of imide carbonyl group: regioselective synthesis of isoindoloisoquinolinone alkaloid (\(\pm )\)-nuevamine. Org Biomol Chem 9:7643–7646. https://doi.org/10.1039/C1OB06349A
Liu CT, Wang QW, Wang CH (1981) Structure of koumine. J Am Chem Soc 103:4634–4635. https://doi.org/10.1021/ja00405a081
Verbitski SM, Mayne CL, Davis RA, Concepcion GP, Ireland CM (2002) Isolation, structure determination, and biological activity of a novel alkaloid, perophoramidine, from the philippine ascidian perophora namei. J Org Chem 67:7124–7126. https://doi.org/10.1021/jo026012f
Siengalewicz P, Gaich T, Mulzer J (2008) It all began with an error: the nomofungin/communesin story. Angew Chem Int Ed 47:8170–8176. https://doi.org/10.1002/anie.200801735
Dalsgaard PW, Blunt JW, Frisvad JC, Christophersen C (2005) Communesins G and H, new alkaloids from the psychrotolerant fungus penicillium rivulum. J Nat Prod 68:258–261. https://doi.org/10.1021/np049646l
Zuo Z, Xie W, Ma D (2010) Total synthesis and absolute stereochemical assignment of (-)-communesin F. J Am Chem Soc 132:13226–13228. https://doi.org/10.1021/ja106739g
Fuchs JR, Funk RL (2004) Total synthesis of (+)-perophoramidine. J Am Chem Soc 126:5068–5069. https://doi.org/10.1021/ja049569g
Wu H, Xue F, Xiao X, Qin Y (2010) Total synthesis of (+)-perophoramidine and determination of the absolute configuration. J Am Chem Soc 132:14052–14054. https://doi.org/10.1021/ja1070043
Modha SG, Vachhani DD, Jacobs J, Sharma SK, Parmar VS, Meervelt LV, Van der Eycken EV (2012) A diversity-oriented approach to spiroindolines: post-Ugi gold-catalyzed diastereoselective domino cyclization. Angew Chem Int Ed 51:9572–9575. https://doi.org/10.1002/anie.201205052
Schröder F, Ojeda M, Erdmann N, Jacobs J, Luque R, Noël T, Meervelt LV, Van der Eyckend J, Van der Eycken E (2015) Supported gold nanoparticles as efficient and reusable heterogeneous catalyst for cycloisomerization reactions. Green Chem 17:3314–3317. https://doi.org/10.1039/C5GC00430F
El Kaïm L, Grimaud L, Le Goff XF, Menes-Arzate M, Miranda LD (2011) Straightforward four-component access to spiroindolines. Chem Commun 47:8145–8147. https://doi.org/10.1039/C1CC12236C
Wang W, Herdtweck E, Domling A (2010) Polycyclic indole alkaloid-type compounds by MCR. Chem Commun 46:770–772. https://doi.org/10.1039/B917660H
Flanagan SR, Harrowven DC, Bradley M (2003) Radical cyclisation reactions with indoles. Tetrahedron Lett 44:1795–1798. https://doi.org/10.1016/S0040-4039(03)00094-7
Miranda LD, CruzAlmanza R, Pavon M, Romero Y, Muchowski JM (2000) A tandem radical addition/cyclization process of 1-(2-iodoethyl)indoles and methyl acrylate. Tetrahedron Lett 35:8433–8436. https://doi.org/10.1016/S0040-4039(00)01829-3
Bennasar ML, Roca T, Griera R, Bosch J (2001) New cascade 2-indolylacyl radical addition–cyclization reactions. J Org Chem 66:7547–7551. https://doi.org/10.1021/jo015905p
Saya JM, Oppelaar B, Cioc RC, Heijden GVD, Vande Velde CML, Orru RVA, Ruijter E (2016) Synthesis of polycyclic spiroindolines by highly diastereoselective interrupted Ugi cascade reactions of 3-(2-isocyanoethyl)indoles. Chem Commun 52:12482–12485. https://doi.org/10.1039/C6CC07459F
Li ZH, Kumar A, Peshkov A, Van der Eycken EV (2016) A domino Ugi/Michael approach for the synthesis of \(\alpha \),\(\beta \)-unsaturated \(\gamma \)-lactams. Tetrahedron Lett 57:754–756. https://doi.org/10.1016/j.tetlet.2016.01.014
Katritzky AR, Rees CW, Scriven EFV (1996) Comprehensive heterocyclic chemistry II, 3rd edn. Pergamon, New York
Tuba R (2013) Synthesis of \(\beta \)-lactams by transition metal promoted Staudinger reactions: alternative synthetic approaches from transition metal enhanced organocatalysis to in situ, highly reactive intermediate synthesis and catalytic tandem reactions. Org Biomol Chem 11:5976–5988. https://doi.org/10.1039/C3OB41048J
Tarui A, Sato K, Omote M, Kumadaki I, Ando A (2010) Stereoselective synthesis of \(\alpha \)-fluorinated amino acid derivatives. Adv Synth Catal 352:2733–2744. https://doi.org/10.1002/adsc.201000506
Pitts CR, Lectka T (2014) Chemical synthesis of \(\beta \)-lactams: asymmetric catalysis and other recent advances. Chem Rev 114:7930–7953. https://doi.org/10.1021/cr4005549
Alcaide B, Almendros P, Luna A (2014) Novel achievements with an old metal: copper-promoted synthesis of four-membered azacycles. RSC Adv 4:1689–1707. https://doi.org/10.1039/C3RA43861A
Adam W, Groer P, Humpf HU, Saha-Möller CR (2000) Synthesis of optically active \(\alpha \)-methylene \(\beta \)-lactams through lipase-catalyzed kinetic resolution. J Org Chem 65:4919–4922. https://doi.org/10.1021/jo0003089
Wang X, Meng F, Wang Y, Han Z, Chen Y, Liu L, Wang Z, Ding K (2012) Aromatic spiroketal bisphosphine ligands: palladium-catalyzed asymmetric allylic amination of racemic Morita–Baylis–Hillman adducts. Angew Chem Int Ed 51:9276–9282. https://doi.org/10.1002/anie.201204925
Li W, Liu C, Zhang H, Ye K, Zhang G, Zhang W, Duan Z, You S, Lei A (2014) Palladium-catalyzed oxidative carbonylation of \(N\)-allylamines for the synthesis of \(\beta \)-lactams. Angew Chem Int Ed 53:2443–2446. https://doi.org/10.1002/anie.201309081
Li ZH, Sharma UK, Liu Z, Sharma N, Harvey JN, Van der Eycken EV (2015) Diversity-oriented synthesis of \(\beta \)-lactams and \(\gamma \)-lactams by post-Ugi nucleophilic cyclization: Lewis acids as regioselective switch. Eur J Org Chem 2015:3957–3962. https://doi.org/10.1002/ejoc.201500270
Yugandhar D, Kuriakose S, Nanubolu JB, Srivastava AK (2016) Synthesis of alkaloid-mimicking tricyclic skeletons by diastereo- and regioselective Ugi/ipso-cyclization/aza-Michael cascade reaction in one-pot. Org Lett 18:1040–1043. https://doi.org/10.1021/acs.orglett.6b00164
Rodriguez-Solla H, Concellon C, Tuya P, Garcia-Granda S, Diaz MR (2012) Asymmetric construction of quaternary stereocenters: synthesis of enantiopure amino acid-based tricyclic \(\alpha \),\(\beta \)-enones through an ipso-Friedel-Crafts/Michael addition cascade. Adv Synth Catal 354:295–300. https://doi.org/10.1002/adsc.201100497
Williams RM, Cox RJ (2003) Paraherquamides, brevianamides, and asperparalines: laboratory synthesis and biosynthesis. An interim report. Acc Chem Res 36:127–139. https://doi.org/10.1021/ar020229e
Zhou F, Liu YL, Zhou J (2010) Catalytic asymmetric synthesis of oxindoles bearing a tetrasubstituted stereocenter at the C-3 position. Adv Synth Catal 352:1381–1407. https://doi.org/10.1002/adsc.201000161
Ball-Jones NR, Badillo JJ, Franz AK (2012) Strategies for the enantioselective synthesis of spirooxindoles. Org Biomol Chem 10:5165–5181. https://doi.org/10.1039/C2OB25184A
Singh GS, Desta ZY (2012) Isatins as privileged molecules in design and synthesis of spiro-fused cyclic frameworks. Chem Rev 112:6104–6155. https://doi.org/10.1021/cr300135y
Hong L, Wang R (2013) Recent advances in asymmetric organocatalytic construction of \(3,3^\prime \)-spirocyclic oxindoles. Adv Synth Catal 355:1023–1052. https://doi.org/10.1002/adsc.201200808
Santos MMM (2014) Recent advances in the synthesis of biologically active spirooxindoles. Tetrahedron 70:9735–9757. https://doi.org/10.1016/j.tet.2014.08.005
Yu B, Yu DQ, Liu HM (2015) Spirooxindoles: promising scaffolds for anticancer agents. Eur J Med Chem 97:673–698. https://doi.org/10.1016/j.ejmech.2014.06.056
Companyó X, Zea A, Alba ANR, Mazzanti A, Moyano A, Rios R (2010) Organocatalytic synthesis of spiro compounds via a cascade Michael–Michael–aldol reaction. Chem Commun 46:6953–6955. https://doi.org/10.1039/C0CC01522A
Wang LL, Peng L, Bai JF, Huang QC, Xu XY, Wang LX (2010) Highly organocatalytic asymmetric Michael-ketone aldol-dehydration domino reaction: straightforward approach to construct six-membered spirocyclic oxindoles. Chem Commun 46:8064–8066. https://doi.org/10.1039/C0CC03032E
Tan B, Hernández-Torres G, Barbas CF III (2011) Highly efficient hydrogen-bonding catalysis of the Diels–Alder reaction of 3-vinylindoles and methyleneindolinones provides carbazolespirooxindole skeletons. J Am Chem Soc 133:12354–12357. https://doi.org/10.1021/ja203812h
Dandia A, Parewa V, Jain AK, Rathore KS (2011) Step-economic, efficient, ZnS nanoparticle-catalyzed synthesis of spirooxindole derivatives in aqueous medium via Knoevenagel condensation followed by Michael addition. Green Chem 13:2135–2145. https://doi.org/10.1039/C1GC15244K
Han-Ya Y, Tokuyama H, Fukuyama T (2011) Total synthesis of (-)-conophylline and (-)-conophyllidine. Angew Chem Int Ed 50:4884–4887. https://doi.org/10.1002/anie.201100981
Li ZH, Sharma N, Sharma UK, Jacobs J, Meerveltb LV, Van der Eycken EV (2016) Ligand-controlled product selectivity in palladium-catalyzed domino post-Ugi construction of (spiro)polyheterocycles. Chem Commun 52:5516–5519. https://doi.org/10.1039/C6CC00784H
Sharma N, Li Z, Sharma UK, Van der Eycken EV (2014) Facile access to functionalized spiro[indoline-3,2\({}^\prime \)-pyrrole]-2,5\({}^\prime \)-diones via post-Ugi domino Buchwald-Hartwig/Michael reaction. Org Lett 16:3884–3887. https://doi.org/10.1021/ol5019079
Li ZH, Zhao YP, Tian GL, He Y, Song GH, Van der Eycken EV (2016) Synthesis of novel imidazole-based triheterocycles via a domino Ugi/Michael reaction and silver-catalyzed heteroannulation. RSC Adv 6:103601–103605. https://doi.org/10.1039/C6RA23180B
Klapars A, Parris S, Anderson KW, Buchwald SL (2004) Synthesis of medium ring nitrogen heterocycles via a tandem copper-catalyzed C–N bond rormation-ring-expansion process. J Am Chem Soc 126:3529–3533. https://doi.org/10.1021/ja038565t
Chattopadhyay SK, Karmakar S, Biswas T, Majumdar KC, Rahaman H, Roy B (2007) Formation of medium-ring heterocycles by diene and enyne metathesis. Tetrahedron 63:3919–3952. https://doi.org/10.1016/j.tet.2007.01.063
Lam JK, Schmidt Y, Vanderwal CD (2012) Complex polycyclic scaffolds by metathesis rearrangement of Himbert arene/allene cycloadducts. Org Lett 14:5566–5569. https://doi.org/10.1021/ol302680m
Lam JK, Pham HV, Houk KN, Vanderwal CD (2013) Computation and experiment reveal that the ring-rearrangement metathesis of Himbert cycloadducts can be subject to kinetic or thermodynamic control. J Am Chem Soc 135:17585–17594. https://doi.org/10.1021/ja409618p
Pham HV, Karns AS, Vanderwal CD, Houk KN (2015) Computational and experimental investigations of the formal dyotropic rearrangements of Himbert arene/allene cycloadducts. J Am Chem Soc 137:6956–6964. https://doi.org/10.1021/jacs.5b03718
Cheng GS, He X, Tian L, Chen JW, Li CJ, Jia XS, Li J (2015) Ugi/Himbert arene/allene Diels–Alder cycloaddition to synthesize strained polycyclic skeleton. J Org Chem 80:11100–11107. https://doi.org/10.1021/acs.joc.5b01724
Richey B, Mason KM, Meyers MS, Luesse SB (2016) Rapid access to conformationally-constrained oxatricycles via Ugi–Smiles couplings. Tetrahedron Lett 57:492–494. https://doi.org/10.1016/j.tetlet.2015.12.068
Hande KR, Huwendiek S, Östring C, Portwood N, Roblick UJ, Pawitan Y, Alaiya A, Sennerstam R, Zetterberg A, Auer G (2004) Improved grading of breast adenocarcinomas based on genomic instability. Cancer Res 64:904–909. https://doi.org/10.1158/0008-5472
Watzke M, Schulz K, Johannes K, Ullrich P, Martens J (2008) First synthesis of bi- and tricyclic \(\alpha \),\(\beta \)-unsaturated \(\delta \)-oxacaprolactams from cyclic imines via ring-closing metathesis. Eur J Org Chem 22:3859–3867. https://doi.org/10.1002/ejoc.200800254
Stalling T, Saak W, Martens J (2013) Synthesis of bicyclic thiazolidinethiones and oxazolidinones by water-mediated multicomponent reactions (MCR) and ring-closing metathesis (RCM). Eur J Org Chem 35:8022–8032. https://doi.org/10.1002/ejoc.201301162
Stalling T, Pauly J, Schmidtmann M, Martens J (2014) Multicomponent synthesis of bicyclic thiazolidinethiones and oxazolidinones in water. Eur J Org Chem 4:833–843. https://doi.org/10.1002/ejoc.201301213
Kröger D, Schlüter T, Fischer M, Geibel I, Martens J (2015) Three-component reaction toward polyannulated quinazolinones, benzoxazinones, and benzothiazinones. ACS Combin Sci 17:202–207. https://doi.org/10.1021/co500165a
Kröger D, Brockmeyer F, Kahrs C (2015) A three-component reaction for rapid access to underexplored 1,3-thiazine-2-thiones. Org Biomol Chem 13:7223–7229. https://doi.org/10.1039/C5OB00377F
Martens J, Offermanns H, Scherberich P (1981) Facile synthesis of racemic cysteine. Angew Chem Int Ed Engl 20:668–670. https://doi.org/10.1002/anie.198106681
Hu JF, Schetz JA, Kelly M, Peng JN, Ang KKH, Flotow H, Leong CY, Ng SB, Buss AD, Wilkins SP, Hamann MT (2002) New antiinfective and human 5-HT2 receptor binding natural and semisynthetic compounds from the jamaican sponge smenospongiaaurea. J Nat Prod 65:476–480. https://doi.org/10.1021/np010471e
Segraves NL, Crews P (2005) Investigation of brominated tryptophan alkaloids from two thorectidae sponges: thorectandra and smenospongia. J Nat Prod 68:1484–1488. https://doi.org/10.1021/np0501334
Kochanowska AJ, Rao KV, Childress S, El-Alfy A, Matsumoto RR, Kelly M, Stewart GS, Sufka KJ, Hamann MT (2008) Secondary metabolites from three florida sponges with antidepressant activity. J Nat Prod 71:186–189. https://doi.org/10.1021/np070371u
Nielsen TE, Schreiber SL (2008) Towards the optimal screening collection: a synthesis strategy. Angew Chem Int Ed 47:48–56. https://doi.org/10.1002/anie.200703073
Mitchell JM, Shaw JT (2006) A structurally diverse library of polycyclic lactams resulting from systematic placement of proximal functional groups. Angew Chem Int Ed 45:1722–1726. https://doi.org/10.1002/anie.200503341
Comer E, Rohan E, Deng L, Porco JA Jr (2007) An approach to skeletal diversity using functional group pairing of multifunctional scaffolds. Org Lett 9:2123–2126. https://doi.org/10.1021/ol070606t
O’Leary-Steele C, Pedersen PJ, James T, Lanyon-Hogg T, Leach S, Hayes J, Nelson A (2010) Synthesis of small molecules with high scaffold diversity: exploitation of metathesis cascades in combination with inter- and intramolecular Diels–Alder reactions. Chem Eur J 16:9563–9571. https://doi.org/10.1002/chem.201000707
Bauer RA, DiBlasi CM, Tan DS (2010) The tert-butylsulfinamide lynchpin in transition-metal-mediated multiscaffold library synthesis. Org Lett 12:2084–2087. https://doi.org/10.1021/ol100574y
Marcaurelle LA, Comer E, Dandapani S, Duvall JR, Gerard B, Kesavan S, Lee MD IV, Liu H, Lowe JT, Marie JC, Mulrooney CA, Pandya BA, Rowley A, Ryba TD, Suh BC, Wei J, Young DW, Akella LB, Ross NT, Zhang YL, Fass DM, Reis SA, Zhao WN, Haggarty SJ, Palmer M, Foley MA (2010) An aldol-based build/couple/pair strategy for the synthesis of medium- and large-sized rings: discovery of macrocyclic histone deacetylase inhibitors. J Am Chem Soc 132:16962–16976. https://doi.org/10.1021/ja105119r
Mizoguchi H, Oguri H, Tsuge K, Oikawa H (2009) Divergent and expeditious access to fused skeletons inspired by indole alkaloids and transtaganolides. Org Lett 11:3016–3019. https://doi.org/10.1021/ol901020a
Dömling A (2006) Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106:17–89. https://doi.org/10.1021/cr0505728
Oguri H, Mizoguchi H, Oikawa H, Ishiyama A, Iwatsuki M, Otoguro K, Ōmura S (2012) Parallel and four-step synthesis of natural-product inspired scaffolds through modular assembly and divergent cyclization. Beilstein J Org Chem 8:930–940. https://doi.org/10.3762/bjoc.8.105
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Lei, J., Meng, JP., Tang, DY. et al. Recent advances in the development of polycyclic skeletons via Ugi reaction cascades. Mol Divers 22, 503–516 (2018). https://doi.org/10.1007/s11030-017-9811-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11030-017-9811-2