Evolution of a gram-scale synthesis of (+)-discodermolide

Amos B. Smith, Thomas J. Beauchamp, Matthew J. Lamarche, Michael D. Kaufman, Yuping Qiu, Hirokazu Arimoto, David R. Jones, Kaoru Kobayashi

Research output: Contribution to journalReview articlepeer-review

240 Citations (Scopus)

Abstract

An efficient, highly convergent, stereocontrolled total synthesis of the potent antimitotic agent (+)-discodermolide (1) has been achieved on gram scale. Key elements of the successful strategy include (1) elaboration of three advanced fragments from a common precursor (CP) which embodies the repeating stereochemical triad of the discodermolide backbone, (2) σ-bond installation of the Z trisubstituted olefin, exploiting a modified Negishi cross-coupling reaction, (3) synthesis of a late-stage phosphoniun salt utilizing high pressure, and (4) Wittig installation of the Z disubstituted olefin and the terminal (Z)-diene.

Original languageEnglish
Pages (from-to)8654-8664
Number of pages11
JournalJournal of the American Chemical Society
Volume122
Issue number36
DOIs
Publication statusPublished - 2000 Sep 13
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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