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Volumn 45, Issue 27, 2004, Pages 5243-5246

Formal total synthesis of hemibrevetoxin B by a convergent strategy

Author keywords

Acyl anion equivalent; Convergent synthesis; Hemibrevetoxin B; Natural product synthesis; Polyether

Indexed keywords

BREVETOXIN; ETHER; HEMIBREVETOXIN B; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 2942608179     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.020     Document Type: Article
Times cited : (33)

References (46)
  • 34
    • 2942562806 scopus 로고    scopus 로고
    • 17and 18wasdeterminedbyHPLCanalysisusingchiralcolumns(CHIRALCELAD[DAICEL] for 18,CHIRALCELOD-H[DAICEL]forbenzoateesterof 17)
    • Enantiomeric purity of 17 and 18 was determined by HPLC analysis using chiral columns (CHIRALCEL AD [DAICEL] for 18, CHIRALCEL OD-H [DAICEL] for benzoate ester of 17)
  • 37
    • 2942529411 scopus 로고    scopus 로고
    • note
    • Slight lowering of the enantiomeric purity was observed in the Mitsunobu reaction step
  • 38
    • 2942622647 scopus 로고    scopus 로고
    • Since epoxide 18 was used as it stood (88-92% ee), the optical purity of 4 was same as that of 18. Although the minor enantiomer of 4 produced small amounts of undesired diastereomers, which were inseparable from 25, in the connection reaction with 5, these were facilely separated from 26 at the C-ring cyclization step
    • Since epoxide 18 was used as it stood (88-92% ee), the optical purity of 4 was same as that of 18. Although the minor enantiomer of 4 produced small amounts of undesired diastereomers, which were inseparable from 25, in the connection reaction with 5, these were facilely separated from 26 at the C-ring cyclization step
  • 43
    • 2942568395 scopus 로고    scopus 로고
    • 26toproduceasignificantamountofthecorrespondingC18-exomethylenederivative
    • Prolonged reaction time resulted in elimination of the TBSO group at C18 of 26 to produce a significant amount of the corresponding C18-exomethylene derivative
  • 46
    • 2942531116 scopus 로고    scopus 로고
    • 2, heating,orchangingconcentrationof 28andreagents)showednoeffect
    • 2, heating, or changing concentration of 28 and reagents) showed no effect


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.