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Enantioselective total synthesis of lycopodine.

ABSTRACT: The first enantioselective total synthesis of lycopodine has been completed. Key steps include a highly diastereoselective organocatalyzed cyclization of a keto sulfone to establish the key C7 and C8 stereocenters and a tandem 1,3-sulfonyl shift/intramolecular Mannich cyclization to form the tricyclic core.

SUBMITTER: Yang H

PROVIDER: S-EPMC2528287 | biostudies-literature | 2008 Jul

REPOSITORIES: biostudies-literature

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Enantioselective total synthesis of lycopodine.

Yang Hua H Carter Rich G RG Zakharov Lev N LN

Journal of the American Chemical Society 20080627 29

The first enantioselective total synthesis of lycopodine has been completed. Key steps include a highly diastereoselective organocatalyzed cyclization of a keto sulfone to establish the key C7 and C8 stereocenters and a tandem 1,3-sulfonyl shift/intramolecular Mannich cyclization to form the tricyclic core. ...[more]

PMID: 18582046

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