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The Daphniphyllum Alkaloids: Total Synthesis of (−)-Calyciphylline N

2015; American Chemical Society; Volume: 137; Issue: 10 Linguagem: Inglês

10.1021/ja503899t

1943-2984

Artem Shvartsbart, Amos B. Smith,

Synthetic Organic Chemistry Methods

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.