The asymmetric total synthesis of (+)-cytotrienin A, an ansamycin-type anticancer drug

Yujiro Hayashi, Mitsuru Shoji, Hayato Ishikawa, Junichiro Yamaguchi, Tomohiro Tamura, Hiroki Imai, Yosuke Nishigaya, Kenichi Takabe, Hideaki Kakeya, Hiroyuki Osada

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

(Chemical Equation Presented) A star-studded lineup: (+)-Cytotrienin A was the target of an asymmetric total synthesis featuring an enantioselective aldol reaction, α-aminoxylation, deoxygenation, and a ring-closing metathesis to form the 21-membered macrolactam. This first total synthesis confirms the relative and absolute confguration of the molecule.

Original languageEnglish
Pages (from-to)6657-6660
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number35
DOIs
Publication statusPublished - 2008 Aug 18
Externally publishedYes

Keywords

  • Aldol reaction
  • Asymmetric synthesis
  • Organocatalysis
  • Ring-closing metathesis
  • Total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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    Hayashi, Y., Shoji, M., Ishikawa, H., Yamaguchi, J., Tamura, T., Imai, H., Nishigaya, Y., Takabe, K., Kakeya, H., & Osada, H. (2008). The asymmetric total synthesis of (+)-cytotrienin A, an ansamycin-type anticancer drug. Angewandte Chemie - International Edition, 47(35), 6657-6660. https://doi.org/10.1002/anie.200802079