Synthesis of (+)-juruenolide C:: Use of sequential 5-exo-Digonal radical cyclization, 1,5-intramolecular hydrogen transfer, and 5-endo-trigonal cyclization

被引：17

作者：

Clive, DLJ ^{[1
]}

Ardelean, ES ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 14期

关键词：

D O I：

10.1021/jo010206y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acetylenic alcohol 10 was converted successively into silane 11 and phenylseleno carbonate 14. On treatment with Ph3SnH, the latter undenwent 5-exo-digonal radical cyclization, intramolecular hydrogen transfer, and 5-endo-trigonal cyclization, yielding 15. Conversion of the lactone into the lactol benzyl ether 17, carbon-silicon bond cleavage, and regeneration of the lactone carbonyl gave (+/-)-juruenolide C (1).

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页码：4841 / 4844

页数：4

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