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SmI2-induced reductive cyclizations for the synthesis of cyclic ethers and applications in natural product synthesis

Tadashi Nakataa  
Author affiliations

a Department of Chemistry, Faculty of Science, Tokyo University of Science, 1-3, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
E-mail: nakata@rs.kagu.tus.ac.jp

Abstract

This tutorial review covers SmI2-induced reductive cyclizations of β-alkoxyacrylate, β-alkoxyvinyl sulfone, and β-alkoxyvinyl sulfoxide, as methods for efficient construction of cyclic ethers. These cyclizations were developed as tools to aid in the total synthesis of marine polycyclic ethers, whose complex, synthetically challenging structures and potent bioactivities have attracted the attention of numerous synthetic organic chemists. Applications of the methods to total syntheses of various natural products containing cyclic ether are also described.

Graphical abstract: SmI2-induced reductive cyclizations for the synthesis of cyclic ethers and applications in natural product synthesis

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Article information

https://doi.org/10.1039/B902737H
Submitted
01 Oct 2009
First published
23 Mar 2010
Chem. Soc. Rev., 2010,39, 1955-1972
Article type
Tutorial Review
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SmI2-induced reductive cyclizations for the synthesis of cyclic ethers and applications in natural product synthesis

T. Nakata, Chem. Soc. Rev., 2010, 39, 1955
DOI: 10.1039/B902737H

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