A two-directional approach to a (-)-dictyostatin C11-C23 segment: Development of a highly diastereoselective, kinetically-controlled Meerwein-Ponndorf-Verley reduction

Andrew K. Dilger, Vijay Gopalsamuthiram, Steven D. Burke

Research output: Contribution to journalArticlepeer-review

28 Scopus citations

Abstract

A three-step synthesis of a precursor to the C11-C23 segment of (-)-dictyostatin is described. The sequence features a sonication-assisted, enantioselective double hetero Diels-Alder (HDA) reaction catalyzed by Jacobsen's Cr(III) Schiff base catalyst, followed by a novel, highly diastereoselective Meerwein-Ponndorf-Verley (MPV) reduction of the hydropyranone subunits under kinetic control to yield the bis-(axial alcohol) 4. Generalized studies of both the HDA and MPV methodologies are also described.

Original languageEnglish (US)
Pages (from-to)16273-16277
Number of pages5
JournalJournal of the American Chemical Society
Volume129
Issue number51
DOIs
StatePublished - Dec 26 2007

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