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Volumn 42, Issue 48, 2003, Pages 5996-6000

A Route to the Thapsigargins from (S)-Carvone Providing a Substrate-Controlled Total Synthesis of Trilobolide, Nortrilobolide, and Thapsivillosin F

Author keywords

Asymmetric synthesis; Natural products; Terpenoids; Total synthesis

Indexed keywords

SUBSTRATES; SYNTHESIS (CHEMICAL);

EID: 0346093953     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200353140     Document Type: Article
Times cited : (107)

References (22)
  • 13
    • 0347659597 scopus 로고    scopus 로고
    • note
    • The configuration of C10 and all subsequently formed stereocenters was unambiguously proven by X-ray analysis of 24 and 26 (vide infra).
  • 16
    • 0035825039 scopus 로고    scopus 로고
    • Slow addition of catalyst was required to obtain high yield at low catalyst loading. For examples of enol ether metathesis reactions with Grubbs' Ru catalysts see: J. D. Rainier, J. M. Cox, S. P. Allwein, Tetrahedron Lett. 2001, 42, 179-181; A. Okada, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2001, 42, 8023-8027; V. K. Aggarwal, A. M. Daly, Chem. Commun. 2002, 21, 2490-2491.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 179-181
    • Rainier, J.D.1    Cox, J.M.2    Allwein, S.P.3
  • 17
    • 0035813419 scopus 로고    scopus 로고
    • Slow addition of catalyst was required to obtain high yield at low catalyst loading. For examples of enol ether metathesis reactions with Grubbs' Ru catalysts see: J. D. Rainier, J. M. Cox, S. P. Allwein, Tetrahedron Lett. 2001, 42, 179-181; A. Okada, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2001, 42, 8023-8027; V. K. Aggarwal, A. M. Daly, Chem. Commun. 2002, 21, 2490-2491.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 8023-8027
    • Okada, A.1    Ohshima, T.2    Shibasaki, M.3
  • 18
    • 0036977159 scopus 로고    scopus 로고
    • Slow addition of catalyst was required to obtain high yield at low catalyst loading. For examples of enol ether metathesis reactions with Grubbs' Ru catalysts see: J. D. Rainier, J. M. Cox, S. P. Allwein, Tetrahedron Lett. 2001, 42, 179-181; A. Okada, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2001, 42, 8023-8027; V. K. Aggarwal, A. M. Daly, Chem. Commun. 2002, 21, 2490-2491.
    • (2002) Chem. Commun. , vol.21 , pp. 2490-2491
    • Aggarwal, V.K.1    Daly, A.M.2
  • 19
    • 0346398637 scopus 로고    scopus 로고
    • note
    • Force field calculations suggest that the OTES group blocks the convex face. Using AD mix α, 16 could be obtained as a single diastereomer (matched case).
  • 20
    • 0345767623 scopus 로고    scopus 로고
    • note
    • An inconsequential side product resulting from protecting group migration under the reaction conditions was also observed. As its deprotection also gave tetraol 21, the separation from 20 was not necessary.
  • 21
    • 0346398638 scopus 로고    scopus 로고
    • University of Cambridge, unpublished results
    • E. P. Balskus, University of Cambridge, unpublished results.
    • Balskus, E.P.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.