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

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

J Am Chem Soc. 2015 Mar 18;137(10):3510-9

Authors: Shvartsbart A, Smith AB

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.

PMID: 25756504 [PubMed - indexed for MEDLINE]

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