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Volumn 5, Issue 16, 2003, Pages 2785-2788

Synthesis of muscothiazoles A and B: Critical role of methyl group substitution in RCM-based syntheses of macrocycles

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; MUSCOTHIAZOLE A; MUSCOTHIAZOLE B; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0141520617     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034571i     Document Type: Article
Times cited : (23)

References (40)
  • 13
    • 0141512649 scopus 로고    scopus 로고
    • note
    • Although the racemic compounds 10b and 11b have been used here, their source is citronellic acid, both enantiomers of which are commercially available, so syntheses of enantiomerically pure samples of muscothiazoles are possible with use of this route.
  • 15
    • 0141623906 scopus 로고    scopus 로고
    • note
    • Conditions: slow addition of solutions of 5a [(i) DCM, 7 mM or (ii) DCM, 2 mM] to a solution of the catalyst 6 [(i) 0.25 equiv, 2.8 mM in DCM, Δ, 5 days or (ii) 0.2 equiv, 2.3 mM in DCM, A, 7 days].
  • 20
    • 0031031774 scopus 로고    scopus 로고
    • For formation of "deletion" products, see: (a) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123. (b) Joe, D.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8635.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 123
    • Clark, J.S.1    Kettle, J.G.2
  • 21
    • 0030786787 scopus 로고    scopus 로고
    • For formation of "deletion" products, see: (a) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123. (b) Joe, D.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8635.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 8635
    • Joe, D.1    Overman, L.E.2
  • 24
    • 0141847259 scopus 로고    scopus 로고
    • note
    • We examined the possibility that complexation of the thiazole to the metathesis catalyst was impeding the reaction (J. Org. Chem. 1999, 64, 8275) by repeating the experiment in the presence of 1 equiv of p-toluenesulfonic acid. No difference was observed. The later successful cyclizations of the monomethyl analogues may be taken as support that complexation was not the cause of the problem.
  • 33
    • 0141623905 scopus 로고    scopus 로고
    • note
    • That was a complex structure, where one ethyl-substituted stereoisomer cyclized well and the other did not; the origin of the effect was not so transparent as in our current simpler molecules.
  • 35
    • 0141623904 scopus 로고    scopus 로고
    • note
    • Substrates 12a-d reacted rapidly (average reaction time 3.5 h).
  • 40
    • 0033011059 scopus 로고    scopus 로고
    • and references therein
    • For a recent discussion of the effect of gem-disubstitutions on reaction rates, see: Jung, M. E. Synlett 1999, S1, 843 and references therein.
    • (1999) Synlett , Issue.S1 , pp. 843
    • Jung, M.E.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.