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Volumn 128, Issue 15, 2006, Pages 5292-5299

Evolution of a total synthesis of (-)-kendomycin exploiting a Petasis-Ferrier rearrangement/ring-closing olefin metathesis strategy

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; AROMATIC COMPOUNDS; ASSEMBLY; ISOMERIZATION; OLEFINS; SYNTHESIS (CHEMICAL);

EID: 33646154015     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja060369+     Document Type: Article
Times cited : (91)

References (85)
  • 15
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    • note
    • 2 atropisomerism: (a) Reference 4b.
  • 20
    • 13844276142 scopus 로고    scopus 로고
    • (c) For an extension of this methodology to the conversion of cyclopropyl diols to oxepanes, see: O'Neil, K. E.; Kingree, S. V.; Minbiole, K. P. C. Org. Lett. 2005, 7, 515-517.
    • (2005) Org. Lett. , vol.7 , pp. 515-517
    • O'Neil, K.E.1    Kingree, S.V.2    Minbiole, K.P.C.3
  • 21
    • 4644259961 scopus 로고    scopus 로고
    • (d) For a mechanistically related Prins cyclization entry to tetrahydropyrans, see: Cossey, K. N.; Funk, R. L. J. Am. Chem. Soc. 2004, 126, 12216-12217.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 12216-12217
    • Cossey, K.N.1    Funk, R.L.2
  • 45
    • 33646142248 scopus 로고    scopus 로고
    • note
    • Even though epoxides 5 were previously reported (ref 4a), to the best of our knowledge this is the first account where spectroscopic analysis for these species is provided (see Supporting Information).
  • 63
    • 0001363277 scopus 로고
    • We revisited the synthesis of epoxides 5 at this point with the purpose to obtain epimeric mixtures enriched in the major isomer, that in turn would maximize the yield of 19(S)-27 and thus the yield of macrocycle (+)-30. However, treatment of aldehyde (+)-11 with (R)-(dimethylamino)methylphenyloxosulfoxonium fluoroborate generated 5 as a diastereomeric mixture (3.7:1) in favor of the desired epimer, which we considered only a modest improvement relative to Matteson methylenation. See: (a) Johnson, C. R.; Haake, M.; Schroeck, C. W. J. Am. Chem. Soc. 1970, 92, 6594-6598.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 6594-6598
    • Johnson, C.R.1    Haake, M.2    Schroeck, C.W.3
  • 67
    • 2942589152 scopus 로고    scopus 로고
    • Macrocyclization to access a variety of small and medium rings via RCM that generate olefins with a dense substitution pattern have been documented but were unprecedented in 16-membered or larger rings. For a recent review on RCM, see: Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238.
    • (2004) Chem. Rev. , vol.104 , pp. 2199-2238
    • Deiters, A.1    Martin, S.F.2
  • 72
    • 33646157237 scopus 로고    scopus 로고
    • note
    • 1H NMR of the reaction mixture revealed a doublet of low intensity at 5.05 ppm (J = 10.1 Hz), characteristic of the vinyl proton expected in 35; correct mass for the RCM product was observed by LRMS.
  • 73
    • 33646147753 scopus 로고    scopus 로고
    • note
    • A NOESY cross-peak was also observed between the methyl of the 4-OTBS group and the C(5)-H benzylic proton in (+)-36, supporting a C(4)-OTBS-C(5)-H synclinal orientation.
  • 74
    • 33646129856 scopus 로고    scopus 로고
    • note
    • COSY and NOESY NMR experiments were employed to assign the regio- and stereochemistry of the C(14,15) e-olefin 37.
  • 83
    • 33646136620 scopus 로고    scopus 로고
    • note
    • 1H NMR signals distinct from those of (-)-42, indicating that the two samples were isomers.
  • 85
    • 0037035044 scopus 로고    scopus 로고
    • For a related example of acid-catalyzed hydrolysis of a vinylogous methyl ester in a p-quinone system, see: Ling, T.; Poupon, E.; Rueden, E. J.; Theodorakis, E. A. Org. Lett. 2002, 4, 819-902.
    • (2002) Org. Lett. , vol.4 , pp. 819-902
    • Ling, T.1    Poupon, E.2    Rueden, E.J.3    Theodorakis, E.A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.