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

41 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

Fingerprint

Rifabutin
Pharmaceutical Preparations
Stars
Molecules
cytotrienin A
3-hydroxybutanal

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Medicine(all)

Cite this

Hayashi, Y., Shoji, M., Ishikawa, H., Yamaguchi, J., Tamura, T., Imai, 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

The asymmetric total synthesis of (+)-cytotrienin A, an ansamycin-type anticancer drug. / Hayashi, Yujiro; Shoji, Mitsuru; Ishikawa, Hayato; Yamaguchi, Junichiro; Tamura, Tomohiro; Imai, Hiroki; Nishigaya, Yosuke; Takabe, Kenichi; Kakeya, Hideaki; Osada, Hiroyuki.

In: Angewandte Chemie - International Edition, Vol. 47, No. 35, 18.08.2008, p. 6657-6660.

Research output: Contribution to journalArticle

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, vol. 47, no. 35, pp. 6657-6660. https://doi.org/10.1002/anie.200802079
Hayashi, Yujiro ; Shoji, Mitsuru ; Ishikawa, Hayato ; Yamaguchi, Junichiro ; Tamura, Tomohiro ; Imai, Hiroki ; Nishigaya, Yosuke ; Takabe, Kenichi ; Kakeya, Hideaki ; Osada, Hiroyuki. / The asymmetric total synthesis of (+)-cytotrienin A, an ansamycin-type anticancer drug. In: Angewandte Chemie - International Edition. 2008 ; Vol. 47, No. 35. pp. 6657-6660.
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