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The daphniphyllum alkaloids: total synthesis of (-)-calyciphylline N.

ABSTRACT: Presented here is a full account on the development of a strategy culminating in the first total synthesis of the architecturally complex daphniphyllum alkaloid, (-)-calyciphylline N. Highlights of the approach include a highly diastereoselective, intramolecular Diels-Alder reaction of a silicon-tethered acrylate; an efficient Stille carbonylation of a sterically encumbered vinyl triflate; a one-pot Nazarov cyclization/proto-desilylation sequence; and the chemoselective hydrogenation of a fully substituted diene ester.

SUBMITTER: Shvartsbart A

PROVIDER: S-EPMC4394112 | biostudies-literature | 2015 Mar

REPOSITORIES: biostudies-literature

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The daphniphyllum alkaloids: total synthesis of (-)-calyciphylline N.

Shvartsbart Artem A Smith Amos B AB

Journal of the American Chemical Society 20150310 10

Presented here is a full account on the development of a strategy culminating in the first total synthesis of the architecturally complex daphniphyllum alkaloid, (-)-calyciphylline N. Highlights of the approach include a highly diastereoselective, intramolecular Diels-Alder reaction of a silicon-tethered acrylate; an efficient Stille carbonylation of a sterically encumbered vinyl triflate; a one-pot Nazarov cyclization/proto-desilylation sequence; and the chemoselective hydrogenation of a fully ...[more]

PMID: 25756504

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