Abbreviated synthesis of the C3-C14 (substituted 1,7-dioxaspiro[5.5]undec-3-ene) system of okadaic acid

被引：17

作者：

Dounay, AB ^{[1
]}

Forsyth, CJ ^{[1
]}

机构：

[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 03期

关键词：

D O I：

10.1021/ol9906615

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Described is a novel, concise, and flexible synthesis of the C3-C14 portion of okadaic acid. A substituted valerolactone (C3-C8) was prepared in three steps and cr-hydroxylated using Davis' oxaziridine, Conjugate addition of dimethylcuprate upon ynones derived from the C3-C8 lactones followed by intramolecular ketalization provided the C3-C14 fragment and revealed a significant role of the C7 alpha' ketone substituent upon the efficiency of spiroketalization.

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页码：451 / 453

页数：3

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