Abstract
A study towards diversity-oriented synthesis of optically active cyclopentane fused bicyclic frameworks has been accomplished. The common intermediate was prepared from commercially available starting material (S)-carvone. The observations on competition between Grubbs-II catalyzed ring closing metathesis (RCM) and ring closing carbonyl-olefin metathesis (RCCOM) were the key features of the study.
A study towards diversity-oriented synthesis of optically active cyclopentane fused bicyclic frameworks has been accomplished. The observations on competition between Grubbs-II catalyzed ring closing metathesis (RCM) and ring closing carbonyl-olefin metathesis (RCCOM) were the key features of the study.
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(a) Burke M D and Schreiber S L 2004 Angew. Chem. Int. Ed. 43 46; (b) Spring D R 2005 Chem. Soc. Rev. 34 472; (c) Tan D S 2005 Nat. Chem. Biol. 1 74; (d) Boethling R S, Sommer E and Di Fiore D 2007 Chem. Rev. 107 2207; (e) Thomas J R and Hergenrother P J 2008 Chem. Rev. 108 1171; (f) Bauer A J and Stockwell B R 2008 Chem. Rev. 108 1774; (g) Schreiber S L 2011 Proc. Natl. Acad. Sci. U.S.A. 108 6699 and references cited therein
Hoelder S, Clarke P A and Workman P 2012 Mol. Oncol. 6 155
Shang S and Tan D S 2005 Curr. Opinion Chem. Biol. 3 248; (b) Cordier C, Morton D, Murrison S, Nelson A and O’Leray-Steele C 2008 Nat. Prod. Rep. 4 719
(a) Devon T K and Scott A I 1972 In Handbook of Naturally Occurring Compounds Vol. II (Academic Press: New York and London); (b) Oishi T, Ohtsuka Y and Rahman A 1989 Stud. Nat. Prod. Chem. 3 73; (c) Faulkner D J 2000 Nat. Prod. Rep. 17 1 and references cited therein
Larry Y 2000 Chem. Rev. 100 2963
(a) Burke M D and Schreiber S L 2004 Angew. Chem., Int. Ed. 43 46; (b) Thomas G L, Wyatt E E and Spring D R 2006 Curr. Opin. Drug Discovery Dev. 9 700; (c) Nielsen T E and Schreiber S L 2008 Angew. Chem. Int. Ed. 47 48; (d) Spandl R J, Spring D R and Bender A 2008 Org. Biomol. Chem. 6 1149
(a) Chen C, Li X, Neumann C S, Lo M M C and Schreiber S L 2005 Angew. Chem. Int. Ed. 44 2249; (b) Lu K, Huang M, Xiang Z, Liu Y, Chen J and Yang Z 2006 Org. Lett. 8 1193; (c) Kotha S and Singh Kuldeep 2007 Eur. J. Org. Chem. 5909; (d) Spandl R J, Rudyk H and Spring D R 2008 Chem. Commun. 3001; (e) Cordier C, Morton D, Murrison S, Nelson A and O’Leary-Steele C 2008 Nat. Prod. Rep. 25 719; (f) Krishna P R and Reddy P S 2008 J. Comb. Chem. 1 426; (g) Lalli C, Trabocchi A, Sladojevich A, Menchi G and Guarna A 2009 Chem. Eur. J. 15 7871; (h) Dandapani S and Marcaurelle L A 2010 Curr. Opin. Chem. Biol. 14 362; (i) Robbins D, Newton A F, Gignoux C, Legeay J-C, Sinclair A, Rejzek M, Laxon C A, Yalamanchili S K, Lewis W, O’Connell M A and Stockman R A 2011 Chem. Sci. 2 2232; (j) Dandapani S, Lowe J T, Comer E and Marcaurelle L A 2011 J. Org. Chem. 76 8042; (k) Hung A W, Ramek A, Wang Y, Kaya T, Wilson J A, Clemons P A and Young D W 2011 Proc. Natl. Acad. Sci. U.S.A. 108 6799; (l) Madsen C M and Clausen M H 2011 Eur. J. Org. Chem. 3107; (m) Dhara K, Midya G C and Dash J 2012 J. Org. Chem. 77 8071; (n) Lenci E, Menchi G, Guarna A and Trabocchi A 2015 J. Org. Chem. 80 2182
(a) Mukherjee P, Roy S J S and Sarkar T K 2010 Org. Lett. 12 2472; (b) Mao B, Fañanás-Mastral M, Lutz M and Feringa B L 2013 Chem. Eur. J. 19 761
(a) Mehta G and Reddy A V 1981 J. Chem. Soc., Chem. Commun. 756; (b) Huneck S, Baxter G, Cameron A F, Connolly J D and Rycroft D S 1983 Tetrahedron Lett. 24 3787; (c) Paquette L A and Annis G D 1983 J. Am. Chem. Soc. 105 7358; (d) Mehta G, Murthy A N, Reddy D S and Reddy A V 1986 J. Am. Chem. Soc. 108 3443; (e) Harrowven D C, Lucas M C and Howes P D 2000 Tetrahedron Lett. 41 8985; (f) Krafft M E, Cheung Y Y and Abboud K A 2001 J. Org. Chem. 66 7443; (g) Clive D L J, Sannigrahi M and Hisaindee S 2001 J. Org. Chem. 66 954; (h) Winkler J D, Rouse M B, Greaney M F, Harrison S J and Jeon Y T 2002 J. Am. Chem. Soc. 124 9726; (i) Heckrodt T J and Muljer J 2003 J. Am. Chem. Soc. 125 4680; (j) Zanoni G and Franzini M 2004 Angew. Chem. Int. Ed. 43 4837; (k) Miller A K, Hughes C C, Kennedy-Smith J J, Gradl S N and Trauner D 2006 J. Am. Chem. Soc. 128 17057; (l) Pallerla M K and Fox J M 2007 Org. Lett. 9 5625; (m) Clive D L J and Liu D 2008 J. Org. Chem. 73 3078; (n) Chen C-H, Chen Y-K and Sha C-K 2010 Org. Lett. 12 1377; (o) Kim H, Bae H, Kim S, Kim D, Lee D and Paton R S 2011 Tetrahedron 67 10017; (p) Liang Y, Jiang X and Yu Z-X 2011 Chem. Commun. 47 6659; (q) Tiong E A, Rivalti D, Williams B M and Gleason J L 2013 Angew. Chem. Int. Ed. 52 3442; (r) Jørgensen L, Mckerrall S J, Kuttraff C A, Ungeheuer F, Felding J and Baran P S 2013 Science 341 878
For selected reviews see: (a) Ivin F J 1983 In Olefin Metathesis (Academic Press: London); (b) Schmalz H G 1995 Angew. Chem. Int. Ed. 34 1833; (c) Grubbs R H, Miller S J and Fu G C 1995 Acc. Chem. Res. 28 446; (d) Grubbs R H and Chang S 1998 Tetrahedron 54 4413; (e) Schuster M and Blechert S 1997 Angew. Chem. Int. Ed. 36 2036; (f) Schrock R R 1999 Tetrahedron 55 8141; (g) Fürstner A 2000 Angew. Chem. Int. Ed. 39 3012; (h) Schrock R R and Hoveyda A H 2003 Angew. Chem. Int. Ed. 42 4592; (i) Deiters A and Martin S F 2004 Chem. Rev. 104 2199; (j) Tori M and Mizutani R 2010 Molecules 15 4242; (k) Blanchard N and Eustache J 2010 In Metathesis in Natural Product Synthesis: Strategies, Substrates and Catalyst (Weinheim: Wiley-VCH)
Fu G C and Grubbs R H 1993 J. Am. Chem. Soc. 115 3800
(a) Oliver S F, Högenauer K, Simic O, Antonello A, Smith M D and Ley S V 2003 Angew. Chem. Int. Ed. 42 5996; (b) Ley S V, Antonello A, Balskus E P, Booth D T, Christensen S B, Cleator E, Gold H, Högenauer K, Hünger U, Myers R M, Oliver S F, Simic O, Smith M D, Søhoel H and Woolford A J A 2004 Proc. Natl. Acad. Sci. U.S.A. 101 12073
(a) Griffith A K, Vanos C M and Lambert T H 2012 J. Am. Chem. Soc. 134 18581 and references cited therein; (b) Ludwig J R, Zimmerman P M, Gianino J B and Schindler C S 2016 Nature 533 374; (c) Ma L, Li W, Xi H, Bai X, Ma E, Yan X and Li Z 2016 Angew. Chem. Int. Ed. 55 10410
For selected reviews on synthesis of oxygen heterocycles, see: (a) Deiters A and Martin S F 2004 Chem. Rev. 104 2199; (b) Grimwood M E and Hansen H C 2009 Tetrahedron 65 8132; (c) Kotha S, Srinivas V and Krishna N G 2012 Heterocycles 86 1555
Acknowledgements
Authors thank Mr. S Mukherjee, Department of Chemistry, Indian Institute of Technology, Kharagpur, West Bengal 721 302, India and A Chadha, Polyplex Corporation Limited, Sector 1, Noida, Uttar Pradesh 201 301, India for help in the preparation of known starting materials during their (SM and AC) summer project training.
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Copies of NMR spectra of new compounds are available in Supplementary Information at www.ias.ac.in/chemsci.
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CHAKRABORTY, P., ROY, S.C. Study towards diversity oriented synthesis of optically active substituted cyclopentane fused carbocyclic and oxacyclic medium-sized rings: Competition between Grubbs-II catalyzed ring closing olefin metathesis and ring closing carbonyl-olefin metathesis. J Chem Sci 128, 1831–1840 (2016). https://doi.org/10.1007/s12039-016-1197-7
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DOI: https://doi.org/10.1007/s12039-016-1197-7