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

Jun Ho Maeng, Raymond L. Funk

Research output: Contribution to journalArticle

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Abstract

(Equation Presented) 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.

Original languageEnglish (US)
Pages (from-to)331-333
Number of pages3
JournalOrganic Letters
Volume4
Issue number3
DOIs
StatePublished - Feb 7 2002

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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