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A biomimetic strategy to access the silybins: total synthesis of (-)-isosilybin A.

ABSTRACT: We report the first asymmetric, total synthesis of (-)-isosilybin A. A late-stage catalytic biomimetic cyclization of a highly functionalized chalcone is employed to form the characteristic benzopyranone ring. A robust and flexible approach to this chalcone provides an entry to the preparation of the entire isomeric family of silybin natural products.

SUBMITTER: McDonald BR

PROVIDER: S-EPMC4284651 | biostudies-literature | 2015 Jan

REPOSITORIES: biostudies-literature

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A biomimetic strategy to access the silybins: total synthesis of (-)-isosilybin A.

McDonald Benjamin R BR Nibbs Antoinette E AE Scheidt Karl A KA

Organic letters 20141217 1

We report the first asymmetric, total synthesis of (-)-isosilybin A. A late-stage catalytic biomimetic cyclization of a highly functionalized chalcone is employed to form the characteristic benzopyranone ring. A robust and flexible approach to this chalcone provides an entry to the preparation of the entire isomeric family of silybin natural products. ...[more]

PMID: 25517432

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