Heteroatom-directed reverse Wacker oxidations. Synthesis of the reported structure of (-)-herbaric acid.

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Title

Heteroatom-directed reverse Wacker oxidations. Synthesis of the reported structure of (-)-herbaric acid.

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The University of Auckland Library

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ResearchSpace@Auckland

Description

A microwave-assisted chemoenzymatic resolution has been used to install the C3 stereocenter of the reported structure of the fungal metabolite herbaric acid in high enantiomeric excess. The synthesis and stereochemical assignment was accomplished using a completely regioselective anti-Markovnikov addition of water to vinylphthalide 3, achieved using a heteroatom-directed Wacker oxidation that proceeds with retention of stereochemistry. These results establish that so-called "reverse" Wacker o...

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Format

Research paper

Research format

Journal article

Date created

2010

Creator

Choi, Peter / Sperry, Jonathan / Brimble, Margaret

URL

http://hdl.handle.net/2292/7981

Related subjects

Biological Products / Fungi / Heterocyclic Compounds, 2-Ring / Lactones / Oxidation-Reduction / Stereoisomerism / Substrate Specificity

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