Total synthesis of (+)-dactylolide through an efficient sequential peterson olefination and prins cyclization reaction

被引：155

作者：

Aubele, DL ^{[1
]}

Wan, SY ^{[1
]}

Floreancig, PE ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 22期

关键词：

allylic compounds; asymmetric synthesis; carbocations; natural products; rearrangement;

D O I：

10.1002/anie.200500564

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Key steps in the total synthesis of the macrolide natural product (+)-dactylolide (see formula) include two enantioselective vinylogous Mukaiyama reactions, fragment coupling through acetal formation, a sequential Peterson olefination/ Prins cyclization reaction that proceeds under very mild conditions, and a Mislow-Evans rearrangement to effect the transposition of an allylic alcohol. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

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页码：3485 / 3488

页数：4

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