A new approach to the pancratistatin C-ring from D-Glucose: Ferrier rearrangement, pseudoinversion and Pd-catalyzed cyclizations

Gregory K. Friestad, Bruce Branchaud

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

A Ferrier rearrangement and β-hydroxyketone transposition are key steps in a route to a pancratistatin C-ring precursor. A key feature of the strategy is the pseudoinversion accomplished by β-hydroxyketone transposition, which allows convenient access from methyl α-D-glucopyranoside. Arylations of the C-ring by intramolecular reductive or non-reductive Pd-catalyzed conjugate addition have been demonstrated, utilizing the C1 hydroxyl to deliver the tethered aryl synthon.

Original languageEnglish (US)
Pages (from-to)5933-5936
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number34
DOIs
StatePublished - Aug 1 1997
Externally publishedYes

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Cyclization
Hydroxyl Radical
Glucose
pancratistatin
methylglucoside

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

A new approach to the pancratistatin C-ring from D-Glucose : Ferrier rearrangement, pseudoinversion and Pd-catalyzed cyclizations. / Friestad, Gregory K.; Branchaud, Bruce.

In: Tetrahedron Letters, Vol. 38, No. 34, 01.08.1997, p. 5933-5936.

Research output: Contribution to journalArticle

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