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Asymmetric total synthesis of alkaloids 223A and 6-epi-223A.

ABSTRACT: Concise and asymmetric total synthesis of the title compounds are described. The key ring system was constructed using an intramolecular Schmidt reaction on a norbornenone derivative, which was subsequently subjected to ring-opening metathesis followed by reduction. An unusual isomerization of the C-6 ethyl group afforded the desired stereochemistry of the natural product. The synthesis is readily adaptable to analogue production.

SUBMITTER: Ghosh P

PROVIDER: S-EPMC2751849 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

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Asymmetric total synthesis of alkaloids 223A and 6-epi-223A.

Ghosh Partha P Judd Weston R WR Ribelin Timothy T Aubé Jeffrey J

Organic letters 20090901 18

Concise and asymmetric total synthesis of the title compounds are described. The key ring system was constructed using an intramolecular Schmidt reaction on a norbornenone derivative, which was subsequently subjected to ring-opening metathesis followed by reduction. An unusual isomerization of the C-6 ethyl group afforded the desired stereochemistry of the natural product. The synthesis is readily adaptable to analogue production. ...[more]

PMID: 19739687

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