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

Journal of the American Chemical Society
Artem Shvartsbart, Amos B Smith

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.

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Citations

Feb 16, 2016·The Journal of Organic Chemistry·Amit Kumar ChattopadhyayStephen Hanessian
Feb 26, 2016·Organic Letters·Hua ZhangJian-Min Yue
Mar 15, 2016·Organic Letters·Beatrice RanieriAntonio M Echavarren
Jun 3, 2016·The Journal of Organic Chemistry·Amit Kumar ChattopadhyayStephen Hanessian
Mar 16, 2017·Organic Letters·Jian Long LiJun Yang
Jan 15, 2016·Angewandte Chemie·Amit Kumar ChattopadhyayStephen Hanessian
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Methods Mentioned

BETA
X-ray
NMR

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