Total synthesis of chiral biaryl natural products by asymmetric biaryl coupling

Marisa C. Kozlowski; Barbara J. Morgan; Elizabeth C. Linton

doi:10.1039/B821092F

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Chemical Society Reviews

Issue 11, 2009

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Total synthesis of chiral biaryl natural products by asymmetric biaryl coupling

Marisa C. Kozlowski , Barbara J. Morgan and Elizabeth C. Linton

Chem. Soc. Rev., 2009, 38, 3193-3207

DOI: 10.1039/B821092F
Received 09 Jun 2009, First published on the web 23 Sep 2009
This article is part of the collection: Rapid complexity generation in natural product total synthesis

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Abstract
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This tutorial review highlights the use of catalytic asymmetric 2-naphthol couplings in total synthesis. The types of chirality, chiral biaryl natural products, prior approaches to chiral biaryl natural products, and other catalytic asymmetric biaryl couplings are outlined. The three main categories of chiral catalysts for 2-naphthol coupling (Cu, V, Fe) are described with discussion of their limitations and advantages. Applications of the copper catalyzed couplings in biomimetic syntheses are discussed including nigerone, hypocrellin, calphostin D, phleichrome, and cercosporin.

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Chemical Society Reviews

Total synthesis of chiral biaryl natural products by asymmetric biaryl coupling

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