Abstract
This thesis focuses on the efficient syntheses of indole alkaloids based on gold-catalyzed cascade cyclizations. Total syntheses of these natural products have been achieved using two strategies for the construction of pyrrolocarbazole cores via gold-catalyzed reaction of conjugated diyne or ynamide. This chapter provides an overview of biosynthesis and previous total synthesis of dictyodendrins and vindorosine, then introduced the gold-catalyzed reaction of alkynes.
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References
Tahlan S, Kumar S, Narasimhan B (2019) BMC Chem 13:1–21
Issa S, Prandina A, Bedel N, Rongved P, Yous S, Le Borgne M, Bouaziz Z (2019) J Enzyme Inhib Med Chem 34:1321–1346
Ōmura S, Iwai Y, Hirano A, Nakagawa A, Awaya J, Tsuchiya H, Takahashi Y, Masuma R (1977) J Antibiot 30:275–282
Ōmura S, Sasaki Y, Iwai Y, Takeshima H (1995) J Antibiot 48:535–548
Gorman M, Neuss N, Biemann K (1962) J Am Chem Soc 84:1058–1059
William JM, Lipscomb WN (1965) J Am Chem Soc 87:4963–4964
Ishikawa H, Colby DA, Seto S, Va P, Tam A, Kakei H, Rayl TJ, Hwang I, Boger DL (2009) J Am Chem Soc 131:4904–4916
Schleicher KD, Sasaki Y, Tam A, Kato D, Duncan KK, Boger DL (2013) J Med Chem 56:483–495
Sears JE, Boger DL (2015) Acc Chem Res 48:653–662
Warabi K, Matsunaga S, van Soest RWM, Fusetani N (2003) J Org Chem 68:2765–2770
Zhang H, Conte MM, Khalil Z, Huang X-C, Capon RJ (2012) RSC Adv 2:4209–4214
Zhang W, Ready JM (2017) Nat Prod Rep 34:1010–1034
Fürstner A, Domostoj MM, Scheiper B (2005) J Am Chem Soc 127:11620–11621
Fürstner A, Domostoj MM, Scheiper B (2006) J Am Chem Soc 128:8087–8094
Buchgraber P, Domostoj MM, Scheiper B, Wirtz C, Mynott R, Rust J, Fürstner A (2009) Tetrahedron 65:6519–6534
Zhang W, Ready JM (2016) J Am Chem Soc 138:10684–10692
Hirao S, Sugiyama Y, Iwao M, Ishibashi F (2009) Biosci Biotechnol Biochem 73:1764–1772
Hirao S, Yoshinaga Y, Iwao M, Ishibashi F (2010) Tetrahedron Lett 51:533–536
Yamaguchi AD, Chepiga KM, Yamaguchi J, Itami K, Davies HML (2015) J Am Chem Soc 137:644–647
Okano K, Fujiwara H, Noji T, Fukuyama T, Tokuyama H (2010) Angew Chem Int Ed 49:5925–5929
Tokuyama H, Okano K, Fujiwara H, Noji T, Fukuyama T (2011) Chem Asian J 6:560–572
Liang J, Hu W, Tao P, Jia Y (2013) J Org Chem 78:5810–5815
Tao P, Liang J, Jia Y (2014) Eur J Org Chem 2014:5735–5748
Pitts AK, O’Hara F, Snell RH, Gaunt MJ (2015) Angew Chem Int Ed 54:5451–5455
O’Connor SE, Maresh JJ (2006) Nat Prod Rep 23:532–547
Tatsis EC, Carqueijeiro I (2017) Dugé De Bernonville T, Franke J, Dang TTT, Oudin A, Lanoue A, Lafontaine F, Stavrinides AK, Clastre M, Courdavailt V, O’Connor SE. Nat Commun 8:1–9
Saya JM, Ruijter E, Orru RVA (2019) Chem Eur J 25:8916–8935
Matsumoto KE, Büchi G, Nishimura H (1971) J Am Chem Soc 93:3299–3301
Heureux N, Wouters J, Markó IE (2005) Org Lett 7:5245–5248
Wang Y, Lin J, Wang X, Wang G, Zhang X, Yao B, Zhao Y, Yu P, Lin B, Liu Y, Cheng M (2018) Chem Eur J 24:4026–4032
Kuehne ME, Bornmann WG, Earley WG, Istvan Marko I (1986) M. J Org Chem 51:2913–2927
Elliott GI, Velcicky J, Ishikawa H, Li YK, Boger DL (2006) Angew Chem Int Ed 45:620–622
Sasaki Y, Kato D, Boger DL (2010) J Am Chem Soc 132:13533–13544
Gorin DJ, Toste FD (2007) Nature 446:395–403
Arcadi A (2008) Chem Rev 108:3266–3325
Shapiro ND, Toste FD (2010) Synlett 675–691
Zificsak CA, Mulder JA, Hsung RP, Rameshkumar C, Wei LL (2001) Tetrahedron 57:7575–7606
Dekorver KA, Li H, Lohse AG, Hayashi R, Lu Z, Zhang Y, Hsung RP (2010) Chem Rev 110:5064–5106
Wang X-N, Yeom H-S, Fang L-C, He S, Ma Z-X, Kedrowski BL, Hsung RP (2014) Acc Chem Res 47:560–578
Pan F, Shu C, Ye L-W (2016) Org Biomol Chem 14:9456–9465
Silva C, Faza ON, Luna MM (2019) Front Chem 7:1–22
Couty S, Meyer C, Cossy J (2006) Angew Chem Int Ed 45:6726–6730
Zheng N, Chang Y-Y, Zhang L-J, Gong J-X, Yang Z (2016) Chem Asian J 11:371–375
Asiri AM, Hashmi ASK (2016) Chem Soc Rev 45:4471–4503
Schmidt B, Audörsch S (2016) Org Lett 18:1162–1165
Kramer S, Madsen JLH, Rottländer M, Skrydstrup T (2010) Org Lett 12:2758–2761
Sharp PP, Banwell MG, Renner J, Lohmann K, Willis AC (2013) Org Lett 15:2616–2619
Matsuda Y, Naoe S, Oishi S, Fujii N, Ohno H (2015) Chem Eur J 21:1463–1467
Hirano K, Inaba Y, Watanabe T, Oishi S, Fujii N, Ohno H (2010) Adv Synth Catal 352:368–372
Irikura KK, Goddard WA (1994) J Am Chem Soc 116:8733–8740
Raubenheimer HG, Esterhuysen MW, Timoshkin A, Chen Y, Frenking G (2002) Organometallics 21:3173–3181
Nieto-Oberhuber C, Muñoz MP, Buñuel E, Nevada C, Cárdenas DJ, Echavarren AM (2004) Angew Chem Int Ed 43:2402–2406
Mamane V, Gress T, Krause H, Fürstner A (2004) J Am Chem Soc 126:8654–8655
Luzung MR, Markham JP, Toste FD (2004) J Am Chem Soc 126:10858–10859
Gorin DJ, Davis NR, Toste FD (2005) J Am Chem Soc 127:11260–11261
Shapiro ND, Toste FD (2007) J Am Chem Soc 129:4160–4161
Tokimizu Y, Oishi S, Fujii N, Ohno H (2014) Org Lett 16:3138–3141
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Matsuoka, J. (2020). Introduction. In: Total Synthesis of Indole Alkaloids. Springer Theses. Springer, Singapore. https://doi.org/10.1007/978-981-15-8652-1_1
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