Efficient synthesis of 4-hydroxycyclopentenones: dysprosium(III) triflate catalyzed Piancatelli rearrangements

被引：35

作者：

Fisher, David ^{[1
]}

Palmer, Leoni I. ^{[1
]}

Cook, Jonathan E. ^{[1
]}

Davis, Jessica E. ^{[1
]}

de Alaniz, Javier Read ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

TETRAHEDRON | 2014年 / 70卷 / 27-28期

基金：

美国国家科学基金会;

关键词：

NAZAROV CYCLIZATION; PROSTAGLANDIN;

D O I：

10.1016/j.tet.2014.03.007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4-Hydroxycyclopentenones represent a privileged scaffold in chemical synthesis. A dysprosium(III) trifluoromethanesulfonate catalyzed rearrangement of furylcarbinols to 4-hydroxycyclopentenones via a 4 pi electrocyclization has been developed. The catalytic Piancatelli rearrangement affords a single trans-diastereomer from both aryl and alkyl substituted furylcarbinols. Published by Elsevier Ltd.

引用

页码：4105 / 4110

页数：6

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