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Pyridone annulation via tandem Curtius rearrangement/6?-electrocyclization: total synthesis of (-)-lyconadin C.

ABSTRACT: A concise, enantioselective total synthesis of the Lycopodium alkaloid (-)-lyconadin C was achieved in 12 steps and high overall yield. Key features include construction of a luciduline congener through Mannich-type cyclization and a one-pot, tandem Curtius rearrangement/6?-electrocyclization to fashion the 2-pyridone system of lyconadin C.

SUBMITTER: Cheng X

PROVIDER: S-EPMC3788595 | biostudies-literature | 2013 Aug

REPOSITORIES: biostudies-literature

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Pyridone annulation via tandem Curtius rearrangement/6π-electrocyclization: total synthesis of (-)-lyconadin C.

Cheng Xiayun X Waters Stephen P SP

Organic letters 20130802 16

A concise, enantioselective total synthesis of the Lycopodium alkaloid (-)-lyconadin C was achieved in 12 steps and high overall yield. Key features include construction of a luciduline congener through Mannich-type cyclization and a one-pot, tandem Curtius rearrangement/6π-electrocyclization to fashion the 2-pyridone system of lyconadin C. ...[more]

PMID: 23909645

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