Utilization of a Michael addition: dipolar cycloaddition cascade for the synthesis of (+/-)-cylindricine C

Organic Letters
Andrew C FlickAlbert Padwa

Abstract

A new approach to the marine alkaloid (+/-)-cylindricine C has been devised. The key element of the synthesis consists of a Michael addition/dipolar cycloaddition cascade between 2,3-bis(phenylsulfonyl)-1,3-butadiene and 9-triisopropylsilanyloxy-non-1-en-5-one oxime. The resulting cycloadduct was converted into (+/-)-cylindricine C by a sequence of reactions including a reductive cyclization, intramolecular enolate alkylation, and conjugate addition to introduce the n-hexyl side chain.

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Citations

Nov 20, 2015·Organic Letters·M Greg Tabor, Ryan A Shenvi
Oct 23, 2015·Chemical Communications : Chem Comm·Amit Kumar Chattopadhyay, Stephen Hanessian
Dec 2, 2015·Natural Product Reports·Anastasia HagerDirk Trauner
Mar 21, 2009·Organic & Biomolecular Chemistry·Celia RibesJ Alberto Marco
Jul 2, 2010·Natural Product Reports·Jonathan C Morris, Andrew J Phillips
Oct 17, 2009·Chemical Reviews·Wenyi Zhao
Sep 8, 2011·Organic Letters·Nemai SahaShital K Chattopadhyay
Aug 16, 2011·Organic Letters·Guillaume LapointePhilippe Renaud

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