Novel "reverse Kahne-type glycosylation": Access to O-, N-, and C-linked epipodophyllotoxin conjugates

David B. Berkowitz, Sungjo Choi, Debnath Bhuniya, Richard K. Shoemaker

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

Exposure of epipodophyllotoxin C4-sulfoxides to triflic anhydride, followed by a silyl glycoside, provides a glycoconjugate of the etoposide variety via formal "reverse Kahne glycosylation." To our knowledge, this is the first example of this variant of the Kahne activation method wherein the activating functionality is positioned on the aglycon, rather than on the sugar. Phenols, anilines, or allyl silanes are also efficiently captured at C4, producing the corresponding O-, N-, and C-linked lignan conjugates.

Original languageEnglish (US)
Pages (from-to)1149-1152
Number of pages4
JournalOrganic Letters
Volume2
Issue number8
DOIs
StatePublished - Apr 20 2000

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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