Applications of ortho-Quinone Methides in the Synthesis of Natural Products

doi:10.6023/cjoc201504031

Abstract

ortho-Methylene cyclohexadienones, which are collectivelly referred to as ortho-quinone methides (o-QMs), were first suggested by Fries in 1907. o-QMs are a kind of short-lived and highly reactive versatile intermediates in organic synthesis. The unstability nature of o-QMs is due to their propensity to undergo rapid rearomatisation either by Michael addition of nucleophiles or, often more usefully, by cycloaddition with 2π partners or via oxa-6π-electrocyclisation to give benzopyrans. ortho-Quinone methides were always used in the synthesis of natural products through Michael addition and cycloaddition. As a new member of the family of inherently reactive species, ortho-quinone methides are similar with radicals, carbocations, carbenes, etc. And now using o-QMs to form skeletons of natural products has become a very useful stratergy. This review contains the major application in the synthesis of natural products during 2009 to 2014.

Key words: ortho-quinone methide, natural products, organic synthesis

Cite this article

Ai Wenying, Liao Daohong, Lei Xiaoguang. Applications of ortho-Quinone Methides in the Synthesis of Natural Products[J]. Chin. J. Org. Chem., 2015, 35(8): 1615-1626.

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