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 Branchaud

Research output: Contribution to journalArticle

21 Citations (Scopus)

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
Externally publishedYes

Fingerprint

Cyclization
Glucose
pancratistatin

Keywords

  • Arylation
  • Conformation
  • Cyclitols
  • Heck Reactions

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

An approach to (+)-pancratistatin from D-glucose : A conformational lock solves a stereochemical problem. / Grubb, Lana M.; Dowdy, April L.; Blanchette, Heather S.; Friestad, Gregory K.; Branchaud, Bruce.

In: Tetrahedron Letters, Vol. 40, No. 14, 02.04.1999, p. 2691-2694.

Research output: Contribution to journalArticle

Grubb, Lana M. ; Dowdy, April L. ; Blanchette, Heather S. ; Friestad, Gregory K. ; Branchaud, Bruce. / An approach to (+)-pancratistatin from D-glucose : A conformational lock solves a stereochemical problem. In: Tetrahedron Letters. 1999 ; Vol. 40, No. 14. pp. 2691-2694.
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