An approach to (+)-pancratistatin from D-glucose: A conformational lock solves a stereochemical problem

Lana M. Grubb, April L. Dowdy, Heather S. Blanchette, Gregory K. Friestad, Bruce P. Branchaud

Research output: Contribution to journalArticle

21 Scopus citations

Abstract

In previous work we discovered that reductive Pd-mediated aryl-enone cyclization of an advanced intermediate resulted in epimerization of a critical stereocenter. Analysis of conformational and steric effects could rationalize the result. Based on that analysis it was anticipated that a conformational lock could suppress the undesired epimerization. Results reported herein confirm that expectation.

Original languageEnglish (US)
Pages (from-to)2691-2694
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number14
DOIs
StatePublished - Apr 2 1999

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Keywords

  • Arylation
  • Conformation
  • Cyclitols
  • Heck Reactions

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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