Issue 47, 2014

Comparative perspective and synthetic applications of transition metal mediated oxidative cyclisation of 1,5-dienes towards cis-2,5-disubstituted tetrahydrofurans

Abstract

cis-2,5-Disubstituted tetrahydrofurans constitute the core of several natural products and synthetic analogues which exhibit a broad and interesting range of biological activities. This review highlights a personal perspective and provides a comparative note on the synthesis of cis-2,5-disubstituted tetrahydrofuran rings from 1,5-diene precursors using metal-oxo species. Also, mechanistic insights for these synthetically significant protocols are given and striking examples from the literature are reported, which draw attention towards the scope and synthetic utility of metal oxidants in the domain of cis-2,5-tetrahydrofuran containing bioactive natural product synthesis.

Graphical abstract: Comparative perspective and synthetic applications of transition metal mediated oxidative cyclisation of 1,5-dienes towards cis-2,5-disubstituted tetrahydrofurans

Article information

Article type
Review Article
Submitted
15 Jul 2014
Accepted
02 Oct 2014
First published
03 Oct 2014

Org. Biomol. Chem., 2014,12, 9492-9504

Author version available

Comparative perspective and synthetic applications of transition metal mediated oxidative cyclisation of 1,5-dienes towards cis-2,5-disubstituted tetrahydrofurans

N. S. Sheikh, Org. Biomol. Chem., 2014, 12, 9492 DOI: 10.1039/C4OB01491J

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