Synthetic efforts toward the C22-C36 subunit of halichondrin B utilizing local and imposed symmetry

Valerie A. Keller, Ikyon Kim, Steven D. Burke

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

(Chemical Equation Presented) The C22-C34 portion (2) of halichondrin B was synthesized from meso-symmetric bis-silyl protected cyclopentenediol (7) in 20 steps and 7% overall yield. This was accomplished through a two-directional synthesis/terminus differentiation strategy that proceeded via achiral, mesosymmetric intermediates for eight steps and employed a Pd(0)-mediated asymmetric double cycloetherification to establish both tetrahydropyran rings.

Original languageEnglish
Pages (from-to)737-740
Number of pages4
JournalOrganic Letters
Volume7
Issue number4
DOIs
Publication statusPublished - 2005 Feb 17

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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