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De novo formal synthesis of (-)-apicularen A via an iterative asymmetric hydration sequence.

ABSTRACT: [Structure: see text] A de novo approach to the formal total synthesis of the macrolide natural product (-)-apicularen A has been achieved in 18 steps from achiral starting materials. Both the absolute and relative stereochemistries of apicularen A were introduced by a Sharpless asymmetric dihydroxylation, a pi-allyl-palladium catalyzed reduction, a stereoselective reduction, and a base-promoted transannulation to install the C-9 stereocenter.

SUBMITTER: Li M

PROVIDER: S-EPMC2529256 | biostudies-literature | 2006 Dec

REPOSITORIES: biostudies-literature

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De novo formal synthesis of (-)-apicularen A via an iterative asymmetric hydration sequence.

Li Miaosheng M O'Doherty George A GA

Organic letters 20061201 26

[Structure: see text] A de novo approach to the formal total synthesis of the macrolide natural product (-)-apicularen A has been achieved in 18 steps from achiral starting materials. Both the absolute and relative stereochemistries of apicularen A were introduced by a Sharpless asymmetric dihydroxylation, a pi-allyl-palladium catalyzed reduction, a stereoselective reduction, and a base-promoted transannulation to install the C-9 stereocenter. ...[more]

PMID: 17165936

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