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Volumn 62, Issue 3, 1997, Pages 474-478

Highly diastereoselective synthesis of pederic acid derivatives

Author keywords

[No Author keywords available]

Indexed keywords

IMMUNOSUPPRESSIVE AGENT; MYCALAMIDE A; MYCALAMIDE B; ONNAMIDE A; PEDERIC ACID DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0031025222     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961841k     Document Type: Article
Times cited : (24)

References (43)
  • 10
    • 8044221804 scopus 로고    scopus 로고
    • We refer to the right hand, amine component of the mycalamides as "mycalamine"
    • We refer to the right hand, amine component of the mycalamides as "mycalamine."
  • 24
    • 0001548708 scopus 로고
    • (R,R)-2,3-Epoxybutane ($120/g from Acros Organics) can be synthesized in two steps from (R,R)-2,3-butanediol ($20/g, Aldrich) or in seven steps from dimethyl (S,S)-tartrate: Byrstrom, S.; Hogberg, H. E.; Norin, T. Tetrahedron 1981, 37, 2249.
    • (1981) Tetrahedron , vol.37 , pp. 2249
    • Byrstrom, S.1    Hogberg, H.E.2    Norin, T.3
  • 34
    • 0025108083 scopus 로고
    • Chiral glycolate imide 6 was prepared in 80% yield from (3,4-dimethoxybenzyl)glycolic acid by using the procedure described for the synthesis of the corresponding (p-methoxybenzyl)glycolate-derived imide: Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 7001
    • Evans, D.A.1    Kaldor, S.W.2    Jones, T.K.3    Clardy, J.4    Stout, T.J.5
  • 36
    • 8044234653 scopus 로고    scopus 로고
    • note
    • Formation of the methyl hemiketal is fast under these conditions (<1h). Cleavage of the TBS ether requires the overnight reaction period.
  • 39
    • 8044255558 scopus 로고    scopus 로고
    • note
    • Use of a pH = 6 aqueous phase is critical to the success of this experiment. Substantial decomposition of 3 occurred in experiments in which the pH of the aqueous phase was not carefully controlled.
  • 42
    • 8044221213 scopus 로고    scopus 로고
    • note
    • The yield of the homoallylic alcohol was 74% when the allylation was performed on a 1 g (5 mmol) scale.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.