The Journal of Organic Chemistry

A highly convergent total synthesis of (+)-compactin

GE Keck, DF Kachensky

文献索引：Keck, Gary E.; Kachensky, David F. Journal of Organic Chemistry, 1986 ,  vol. 51,  # 13  p. 2487 - 2493

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被引用次数: 49

摘要

An intramolecular Diels-Alder approach to the construction of (+)-compactin is described. Alkylation of the lithium enolate of (acetylmethy1ene) triphenylphoephorane with the tosylate of allenic alcohol 15 affords phosphorane 16, which condenses with aldehyde 6 (prepared from tri-0-acetyl-D-glucal) to afford enone 3. Intramolecular Diels-Alder reaction, reduction with lithium tri-sec-butylborohydride, and acylation with (S)-(+)-2-methylbutyric anhydride ...