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Volumn 39, Issue 26, 1998, Pages 4647-4650

Intramolecular Heck cyclization of α-sulfenyl enol triflates. Asymmetric synthesis of a pentacyclic cardenolide precursor having functionality at C-11

Author keywords

Aldol reactions; Enantiospecificity; Heck reactions; Sterols; Sulfones

Indexed keywords

CARDENOLIDE; OUABAIN; STEROID; SULFENIC ACID DERIVATIVE; SULFONE DERIVATIVE;

EID: 0032565932     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00860-0     Document Type: Article
Times cited : (39)

References (22)
  • 3
    • 0010464674 scopus 로고    scopus 로고
    • note
    • 3. Intramolecular aldolization has been employed previously to form 14-hydroxy steroids [see references 10-14]. However, to the best of our knowledge, the nucleophilic component has not previously been a 9-keto group.
  • 9
    • 0010422580 scopus 로고    scopus 로고
    • note
    • 9. This mixture undoubtedly arises by indiscriminate formation of a mixture of E- and Z-samarium enolates. This scenario has been rigorously established in a related system. Unpublished studies of M. Jensen of this laboratory.
  • 15
    • 0010462272 scopus 로고    scopus 로고
    • note
    • 15. We have independently demonstrated that the β epimer of 9 is converted to 11 under these conditions. It is notable that 10 can be prepared and cleaved without unraveling to an enone.
  • 16
    • 0010462112 scopus 로고    scopus 로고
    • note
    • 4NSi, MH).
  • 18
    • 0010462838 scopus 로고    scopus 로고
    • note
    • 3NS, M).
  • 19
    • 0010503031 scopus 로고    scopus 로고
    • note
    • 19. The authors have deposited atomic coordinates for this compound with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
  • 20
    • 0010422236 scopus 로고    scopus 로고
    • note
    • 22 in organopalladium reactions has been described.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.