Asymmetric total synthesis of (-)-azaspirene, a novel angiogenesis inhibitor

Yujiro Hayashi, Mitsuru Shoji, Junichiro Yamaguchi, Kenji Sato, Shinpei Yamaguchi, Takasuke Mukaiyama, Ken Sakai, Yukihiro Asami, Hideaki Kakeya, Hiroyuki Osada

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61 Citations (Scopus)

Abstract

The asymmetric total synthesis of (-)-azaspirene, an angiogenesis inhibitor, has been accomplished, establishing its absolute stereochemistry. The key steps are a MgBr2·OEt2-mediated, diastereoselective Mukaiyama aldol reaction, a NaH-promoted, intramolecular cyclization of an alkynylamide, and the aldol reaction of a ketone containing functionalized γ-lactam moiety without protection of tert-alcohol and amide functionalities.

Original languageEnglish
Pages (from-to)12078-12079
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number41
DOIs
Publication statusPublished - Oct 16 2002
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Hayashi, Y., Shoji, M., Yamaguchi, J., Sato, K., Yamaguchi, S., Mukaiyama, T., ... Osada, H. (2002). Asymmetric total synthesis of (-)-azaspirene, a novel angiogenesis inhibitor. Journal of the American Chemical Society, 124(41), 12078-12079. https://doi.org/10.1021/ja0276826