Masked o-benzoquinone strategy in organic synthesis: Short and efficient construction of cis-decalins and linear triquinanes from 2-methoxyphenols-Reference-Cited by-同舟云学术

Masked o-benzoquinone strategy in organic synthesis: Short and efficient construction of cis-decalins and linear triquinanes from 2-methoxyphenols

Published:2005-01-01 Issue:7 Volume:77 Page:1221-1234
ISSN:1365-3075
Container-title:Pure and Applied Chemistry
language:
Short-container-title:

Author:

Liao Chun-Chen¹

Affiliation:

1. 1Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan

Abstract

The inter- and intramolecular Diels–Alder reactions of masked o-benzoquinones generated in situ from the oxidation of easily accessible 2-methoxyphenols with diacetoxyiodobenzene or bis(trifluoroacetoxy)iodobenzene provided cycloadducts in excellent regio- and stereoselectivity and good yields. A general approach to the synthesis of highly substituted cis-decalins and triquinanes with complete stereocontrol from the cycloadducts has been developed. The applicability of our methodology is demonstrated by the total syntheses of several natural products.

Publisher

Walter de Gruyter GmbH

Subject

General Chemical Engineering,General Chemistry

Link

https://www.degruyter.com/document/doi/10.1351/pac200577071221/pdf

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