메뉴 건너뛰기




Volumn 8, Issue 6, 2006, Pages 1117-1120

Enantioselective total synthesis of (-)-dactylolide

Author keywords

[No Author keywords available]

Indexed keywords

DACTYLOLIDE; FUSED HETEROCYCLIC RINGS; LACTONE;

EID: 33646454422     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol053092b     Document Type: Article
Times cited : (55)

References (36)
  • 12
    • 33646450303 scopus 로고    scopus 로고
    • note
    • The enantiomeric excess was determined using chiral HPLC (Chiralcel AD-H, 5% isopropyl alcohol/hexane) by comparison with both enantiomers of the tetrahydropyran 9.
  • 13
    • 33646448329 scopus 로고    scopus 로고
    • note
    • An attempted hetero-Diels-Alder reaction of TBS-protected analogue of enol ether 6 and PMB-protected analogue of aldehyde 7 gave the corresponding pyran in 77% yield but only 66% ee.
  • 16
    • 33646449234 scopus 로고    scopus 로고
    • note
    • Assigned by analogy to the literature (ref 11). Confirmation of this stereochemical assignment was obtained on the synthesis of pyran 4 (see below, refs 15 and 16).
  • 26
    • 33646440196 scopus 로고    scopus 로고
    • note
    • 1H NMR NOESY cross-peak between the C16 alkene proton and the C18 allylic protons.
  • 34
    • 33646446490 scopus 로고    scopus 로고
    • note
    • Inversion of the C19 configuration during the Mitsunobu esterification was confirmed by the synthesis of (-)-dactylolide 1. By contrast, for a route targeting the synthesis of (+)-zampanolide 2 containing a related esterification at C19 that occurs with retention of configuration, see ref 2.
  • 35
    • 33646440902 scopus 로고    scopus 로고
    • note
    • This RCM reaction was inspired by the approach reported by Hoye for a structurally related substrate (ref 5a). In the final stages of this work a similar sequence of steps was applied to compound 24 by Jennings (ref 5b).
  • 36
    • 33646446355 scopus 로고    scopus 로고
    • note
    • D = +30 (c 0.29, MeOH), ref 1.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.