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

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

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter24: Catalytic Carbon-carbon Bond Formation

Section: Chapter Questions

Problem 24.36P

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