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Total synthesis of (-)-calyciphylline N.

ABSTRACT: The total synthesis of the architecturally complex Daphniphyllum alkaloid (-)-calyciphylline N has been achieved. Highlights of the synthesis include a Et2AlCl-promoted, highly stereoselective, susbtrate-controlled intramolecular Diels-Alder reaction, a transannular enolate alkylation, an effective Stille carbonylation/Nazarov cyclization sequence, and a high-risk diastereoselective hydrogenation of a fully substituted conjugated diene ester.

SUBMITTER: Shvartsbart A

PROVIDER: S-EPMC3908864 | biostudies-literature | 2014 Jan

REPOSITORIES: biostudies-literature

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Total synthesis of (-)-calyciphylline N.

Shvartsbart Artem A Smith Amos B AB

Journal of the American Chemical Society 20131209 3

The total synthesis of the architecturally complex Daphniphyllum alkaloid (-)-calyciphylline N has been achieved. Highlights of the synthesis include a Et2AlCl-promoted, highly stereoselective, susbtrate-controlled intramolecular Diels-Alder reaction, a transannular enolate alkylation, an effective Stille carbonylation/Nazarov cyclization sequence, and a high-risk diastereoselective hydrogenation of a fully substituted conjugated diene ester. ...[more]

PMID: 24319987

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