Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Give a mechanism for the first step of the reaction and explain why it goes in the direction it does.

Chapman's (O. L. Chapman, then at Iowa State and later at UCLA) classic total synthe-
sis of (+)-carpanone is so remarkably simple that it is used as an undergraduate labora-
tory preparation. It is modeled on a possible biosynthetic route for this lignan-derived
natural product. Phenol oxidations figure prominently in many such biosyntheses of
natural products. In one step, this reaction creates no less than five contiguous chiral
centers, all in the correct relative configuration.
K* tert-Buo-
DMSO
ОН
HO.
[0]
(+)-Carpanone
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Transcribed Image Text:Chapman's (O. L. Chapman, then at Iowa State and later at UCLA) classic total synthe- sis of (+)-carpanone is so remarkably simple that it is used as an undergraduate labora- tory preparation. It is modeled on a possible biosynthetic route for this lignan-derived natural product. Phenol oxidations figure prominently in many such biosyntheses of natural products. In one step, this reaction creates no less than five contiguous chiral centers, all in the correct relative configuration. K* tert-Buo- DMSO ОН HO. [0] (+)-Carpanone
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