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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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
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Would you expect the product to be racemic or a single enantiomer?

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
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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Stereochemistry is a branch of chemistry that deals with the arrangement of atoms in 3D. It explains the phenomenon of chirality and configuration.

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