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Stereoselective synthesis of the eastern quinolizidine portion of himeradine A.

ABSTRACT: The synthesis of the C(15)-C(17)/N(1')-C(11') quinolizidine portion of himeradine A is disclosed. An intramolecular, heteroatom Michael addition was employed to establish the C(6') stereogenic center with high diastereoselectivity. The quinolizidine ring was constructed using microwave-induced cyclization at the N(1')-C(2') position. The C(17) stereogenic center was introduced through a diastereoselective Overman rearrangement.

SUBMITTER: Collett ND

PROVIDER: S-EPMC3150458 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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Stereoselective synthesis of the eastern quinolizidine portion of himeradine A.

Collett Nathan D ND Carter Rich G RG

Organic letters 20110712 15

The synthesis of the C(15)-C(17)/N(1')-C(11') quinolizidine portion of himeradine A is disclosed. An intramolecular, heteroatom Michael addition was employed to establish the C(6') stereogenic center with high diastereoselectivity. The quinolizidine ring was constructed using microwave-induced cyclization at the N(1')-C(2') position. The C(17) stereogenic center was introduced through a diastereoselective Overman rearrangement. ...[more]

PMID: 21749086

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