Total synthesis and structural revision of callipeltoside C

Joseph Carpenter, Alan B. Northrup, De Michael Chung, John J.M. Wiener, Sung Gon Kim, David W.C. MacMillan

Research output: Contribution to journalArticle

68 Scopus citations

Abstract

(Chemical Equation Presented) Look again: Highlights of the 20-step synthesis of callipeltoside C include the proline-catalyzed direct aldol reaction, enantioselective α-oxyamination reaction, and rapid access to the carbohydrate framework using a de novo synthesis protocol. Based on this work the previously assigned absolute configuration of the pendent 2-O-methylevalose unit has been revised.

Original languageEnglish (US)
Pages (from-to)3568-3572
Number of pages5
JournalAngewandte Chemie - International Edition
Volume47
Issue number19
DOIs
StatePublished - Apr 28 2008

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • Asymmetric synthesis
  • Callipeltoside C
  • Carbohydrates
  • Organocatalysis

Fingerprint Dive into the research topics of 'Total synthesis and structural revision of callipeltoside C'. Together they form a unique fingerprint.

  • Cite this