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The stereochemistry of glabrescol

✍ Scribed by Benjamin R Bellenie; Jonathan M Goodman

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
113 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

The structure of glabrescol has been proposed and revised. Could the revised structure have been predicted without the need for total synthesis? Molecular modelling studies showed that the natural product structure proposed for glabrescol was not the most thermodynamically favourable form. When a lithium ion was incorporated, the natural product proved to be the lowest in energy of all symmetric isomers of glabrescol. Further modelling studies have led to the discovery of an asymmetric isomer lower in energy than the natural product when bound to a variety of ions.

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