1,6-Asymmetric Induction in Boron-Mediated Aldol Reactions: Application to a Practical Total Synthesis of (+)-Discodermolide

Ian Paterson, Gordon John Florence, Oscar Delgado, Isabelle Lyothier, Jeremy P. Scott, Natascha Sereinig

Research output: Contribution to journalArticlepeer-review

88 Citations (Scopus)

Abstract

By relying solely on substrate-based stereocontrol, a practical total synthesis of the microtubule-stabilizing anticancer agent (+)-discodermolide has been realized. This exploits a novel aldol bond construction with 1,6-stereoinduction from the boron enolate of (Z)-enone 3 in addition to aldehyde 2. The 1,3-diol 7 is employed as a common building block for the C-1-C-5, C-9-C-16, and C-17-C-24 subunits.

Original languageEnglish
Pages (from-to)35-38
Number of pages4
JournalOrganic Letters
Volume5
Issue number1
DOIs
Publication statusPublished - 9 Jan 2003

Keywords

  • GRAM-SCALE SYNTHESIS
  • STEREOCONTROLLED SYNTHESIS
  • (-)-DISCODERMOLIDE
  • DISCODERMOLIDE
  • OXIDATION
  • KETONES
  • AGENT
  • MICROTUBULES
  • ALDEHYDES
  • MOLECULES

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