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Volumn 128, Issue 49, 2006, Pages 15851-15855

A general strategy for synthesis of both (6Z)- and (6E)-cladiellin diterpenes: Total syntheses of (-)-cladiella-6,11-dien-3-ol, (+)-polyanthellin A, (-)-cladiell-11-ene-3,6,7-triol, and (-)-deacetoxyalcyonin acetate

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; ESTERS; MOLECULAR DYNAMICS; SYNTHESIS (CHEMICAL);

EID: 33845462422     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja065782w     Document Type: Article
Times cited : (54)

References (60)
  • 33
    • 33845436485 scopus 로고    scopus 로고
    • note
    • In addition, the syn stereochemistry has been shown to play a critical role for controlling the diastereoselectivity of the intramolecular Diels-Alder reaction for construction of the (Z)-cladiellin skeleton (see ref 3e).
  • 39
    • 33845410374 scopus 로고    scopus 로고
    • note
    • (b) A small amount (∼5%) of overoxidized α,α′- alkenediol was obtained.
  • 42
    • 33845468062 scopus 로고    scopus 로고
    • note
    • (b) Use of KHMDS as base did not effect internal alkylation. leading instead to decomposition.
  • 43
    • 33845405800 scopus 로고    scopus 로고
    • Thesis, Seoul National University. Seoul, Korea
    • Kim, J. M.S. Thesis, Seoul National University. Seoul, Korea. 2006.
    • (2006)
    • Kim, J.M.S.1
  • 46
    • 0017814308 scopus 로고
    • (b) Attempt to isomerize the (Z)-enal under the Corey conditions was unsuccessful, leading to decomposition. See: Corey, E. J.; Weigel, L. O.; Floyd, D.; Bock, M. G. J. Am. Chem. Soc. 1978, 100, 2916.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 2916
    • Corey, E.J.1    Weigel, L.O.2    Floyd, D.3    Bock, M.G.4
  • 48
    • 33845446099 scopus 로고    scopus 로고
    • note
    • (b) Use of excess oxidant for a longer time caused allylic oxidation at the reactive (6E)-double bond.
  • 49
    • 33845425296 scopus 로고    scopus 로고
    • note
    • The corresponding tetraene with a benzyl protecting group at C(3) furnished the desired IMDA adduct in an inferior yield of 50%.
  • 53
    • 33845423732 scopus 로고    scopus 로고
    • note
    • (b) Mercuriocyclization-demercuration of a related (6Z)-oxatricycle was shown to be completely nonregioseleetive (see ref 2e).
  • 54
    • 33845447975 scopus 로고    scopus 로고
    • note
    • 4 opening of the resultant β-epoxide (see ref 3f).
  • 56
    • 33845403321 scopus 로고    scopus 로고
    • note
    • Osmylation of a related (6Z)-oxatricycle was shown to be nonstereoselective (see refs 2d,e).
  • 57
    • 33845440996 scopus 로고    scopus 로고
    • note
    • The present synthesis also constitutes a formal synthesis of (-)-sclerophytin A (see ref 2f).
  • 58
    • 33845458992 scopus 로고    scopus 로고
    • note
    • 3 produced oxatetracycle 24 as the major product.
  • 60
    • 33845411358 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.