Total synthesis of (+/-)fasicularin via a 2-amidoacrolein cycloaddition

¹Department of Chemistry, Pennsylvania State University, University Park, PA 16802, USA.

|February 1, 2002

Abstract:

The total synthesis of the cytotoxin fasicularin is described. The key steps include the following: (1) an intermolecular Diels-Alder cycloaddition of a 2-(triflamido)acrolein with the dioxolane ketal of trideca-1,3-dien-7-one to establish the trans-perhydroisoquinoline stereochemistry, (2) a stereoelectronically controlled hydride addition to a N(1)-C(2) iminium ion to introduce the equatorial hexyl substituent, and (3) elaboration of the pyrido ring by an internal aldol reaction.

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Abstract:

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