Total synthesis of (±)-lepadiformine via an amidoacrolein cycloaddition

T. J. Greshock, Raymond Lee Funk

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Abstract

(matrix presented) The total synthesis of the cytotoxin lepadiformine is described. The intermolecular cycloaddition of a 2-amidoacrolein with the dimethyl acetal of 4,6-heptadienal gave a cycloadduct that was strategically functionalized for elaboration of the tricyclic ring system. These steps include a diastereoselective addition of an organoytterbium reagent to an aldehyde, cyclization to the trans-perhydroquinoline substructure via a Mitsunobu reaction, and an iodine-promoted amine cyclization with an alkene to introduce the pyrrolidine ring.

Original languageEnglish (US)
Pages (from-to)3511-3514
Number of pages4
JournalOrganic Letters
Volume3
Issue number22
DOIs
Publication statusPublished - Nov 1 2001

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All Science Journal Classification (ASJC) codes

  • Molecular Medicine

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