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Volumn 74, Issue 24, 2009, Pages 9337-9344

Toward the total synthesis of vinigrol: Synthesis of epi-C-8- dihydrovinigrol

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC ALCOHOL; CATALYTIC HYDROGENATION; CHEMICAL EQUATIONS; FUNCTIONALIZED; REDUCTIVE OPENING; REGIO-SELECTIVE; TERTIARY ALCOHOLS; TOTAL SYNTHESIS; VINIGROL;

EID: 73149102322     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901971f     Document Type: Article
Times cited : (13)

References (36)
  • 5
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    • Jpn. Kokai Tokyo Koho JP 07206668;, 246812
    • (b) Nakajima, H. ; Yamamoto, N. ; Kaisi, T. Jpn. Kokai Tokyo Koho JP 07206668; Chem. Abstr. 1995, 123, 246812.
    • (1995) Chem. Abstr , vol.123
    • Nakajima, H.1    Yamamoto, N.2    Kaisi, T.3
  • 6
    • 34547939638 scopus 로고    scopus 로고
    • Studies toward vinigrol: (a) For a review, see Tessier, G.; Barriault L. Org. Prep. Proc. Int. 2007, 39, 311.
    • Studies toward vinigrol: (a) For a review, see Tessier, G.; Barriault L. Org. Prep. Proc. Int. 2007, 39, 311.
  • 10
    • 73149103568 scopus 로고    scopus 로고
    • Ph.D. Thesis, Harvard University
    • (e) Goodman, S. N. Ph.D. Thesis, Harvard University, 2000.
    • (2000)
    • Goodman, S.N.1
  • 27
    • 73149106260 scopus 로고    scopus 로고
    • The numbering used in this paper refers to the corresponding centers of vinigrol
    • The numbering used in this paper refers to the corresponding centers of vinigrol.
  • 28
    • 77952559966 scopus 로고
    • For a review of thermal cyclization of unsaturated ketones see
    • For a review of thermal cyclization of unsaturated ketones see: Conia, J. M.; Le Perchec, P. Synthesis 1975, 1.
    • (1975) Synthesis , pp. 1
    • Conia, J.M.1    Le Perchec, P.2
  • 29
    • 73149112929 scopus 로고    scopus 로고
    • Initial attempts to carry out the epoxidation of the intermediate alcohol failed; the resulting epoxide rapidly underwent an intramolecular ring opening by the hydroxyl group producing the corresponding cyclic ether
    • Initial attempts to carry out the epoxidation of the intermediate alcohol failed; the resulting epoxide rapidly underwent an intramolecular ring opening by the hydroxyl group producing the corresponding cyclic ether.
  • 30
    • 73149111596 scopus 로고    scopus 로고
    • The ratio of 12 and its epimer 13 depends upon the experimental conditions of the hydrogenation and may vary from 2:3 to 2:1. The best result (2:1) was obtained when the reaction mixture was stirred under hydrogen in the presence of a large amount of catalyst for 17 h (see Supporting Information).
    • The ratio of 12 and its epimer 13 depends upon the experimental conditions of the hydrogenation and may vary from 2:3 to 2:1. The best result (2:1) was obtained when the reaction mixture was stirred under hydrogen in the presence of a large amount of catalyst for 17 h (see Supporting Information).
  • 31
    • 3042662232 scopus 로고    scopus 로고
    • It is known that commercial 10% Pd/C preparations are acidic and exhibit a marked tendency to cleave acid-sensitive alcohols protective groups such as TES or THP ethers. See, for example: Ikawa, T.; Sajiki, H.; Hirota, K. Tetrahedron 2004, 60, 6189.
    • It is known that commercial 10% Pd/C preparations are acidic and exhibit a marked tendency to cleave acid-sensitive alcohols protective groups such as TES or THP ethers. See, for example: Ikawa, T.; Sajiki, H.; Hirota, K. Tetrahedron 2004, 60, 6189.
  • 34
    • 73149087766 scopus 로고    scopus 로고
    • Initial attempts to prepare alcohol 14 from by reductive opening of cyclic carbonate 22 or from the corresponding cyclic sulfate were unsuccessful.
    • Initial attempts to prepare alcohol 14 from by reductive opening of cyclic carbonate 22 or from the corresponding cyclic sulfate were unsuccessful.
  • 35
    • 73149116748 scopus 로고    scopus 로고
    • CCDC 747695, 747694, 747693, 747696, and 747697 (17, 22, 25, 28, and 32, respectively) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge crystallographic Data centre at www.ccdc.com.ac.uk/data/cif.
    • CCDC 747695, 747694, 747693, 747696, and 747697 (17, 22, 25, 28, and 32, respectively) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge crystallographic Data centre at www.ccdc.com.ac.uk/data/cif.
  • 36
    • 72249103425 scopus 로고    scopus 로고
    • While the manuscript was under revision, Baran and coworkers published the first total synthesis of vinigrol. Maimone, T. J, Shi, J, Ashida, S, Baran, P. S. J. Am. Chem. Soc. ASAP October 30 2009, DOI: 10 1021/ja908194b
    • While the manuscript was under revision, Baran and coworkers published the first total synthesis of vinigrol. Maimone, T. J.; Shi, J.; Ashida, S.; Baran, P. S. J. Am. Chem. Soc. ASAP October 30 2009, DOI: 10 1021/ja908194b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.