A NOVEL-APPROACH TO ANGULAR TRIQUINANES VIA INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION OF NITRILE OXIDE

被引：21

作者：

IHARA, M

TOKUNAGA, Y

TANIGUCHI, N

FUKUMOTO, K

KABUTO, C

机构：

[1] TOHOKU UNIV,INST PHARMACEUT,AOBAYAMA,SENDAI 980,JAPAN

[2] TOHOKU UNIV,FAC SCI,INSTRUMENTAL ANAL CTR CHEM,AOBAYAMA,SENDAI 980,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 18期

关键词：

D O I：

10.1021/jo00018a014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The framework of angular triquinane sesquiterpenes was stereoselectively constructed via the intramolecular 1,3-dipolar cycloaddition of nitrile oxide precursors. Optically active indandione 9 was converted into olefinic oximes 18A and 18B through two successive alkylations, followed by ring contraction. Oxidation of the mixture 18A and 18B with sodium hypochlorite gave rise to tetracyclic isoxazolines 21A and 21B, which were transformed into tricyclo[6.3.0.0(4,8)]undecanes 28 and 29.

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页码：5281 / 5285

页数：5

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