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

Research output: Contribution to journalArticle

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 - 2002 Oct 16
Externally publishedYes

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Stereochemistry
Angiogenesis Inhibitors
Cyclization
Ketones
Amides
Alcohols
Lactams
3-hydroxybutanal
azaspirene

ASJC Scopus subject areas

  • Chemistry(all)

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

Asymmetric total synthesis of (-)-azaspirene, a novel angiogenesis inhibitor. / Hayashi, Yujiro; Shoji, Mitsuru; Yamaguchi, Junichiro; Sato, Kenji; Yamaguchi, Shinpei; Mukaiyama, Takasuke; Sakai, Ken; Asami, Yukihiro; Kakeya, Hideaki; Osada, Hiroyuki.

In: Journal of the American Chemical Society, Vol. 124, No. 41, 16.10.2002, p. 12078-12079.

Research output: Contribution to journalArticle

Hayashi, Y, Shoji, M, Yamaguchi, J, Sato, K, Yamaguchi, S, Mukaiyama, T, Sakai, K, Asami, Y, Kakeya, H & Osada, H 2002, 'Asymmetric total synthesis of (-)-azaspirene, a novel angiogenesis inhibitor', Journal of the American Chemical Society, vol. 124, no. 41, pp. 12078-12079. https://doi.org/10.1021/ja0276826
Hayashi Y, Shoji M, Yamaguchi J, Sato K, Yamaguchi S, Mukaiyama T et al. Asymmetric total synthesis of (-)-azaspirene, a novel angiogenesis inhibitor. Journal of the American Chemical Society. 2002 Oct 16;124(41):12078-12079. https://doi.org/10.1021/ja0276826
Hayashi, Yujiro ; Shoji, Mitsuru ; Yamaguchi, Junichiro ; Sato, Kenji ; Yamaguchi, Shinpei ; Mukaiyama, Takasuke ; Sakai, Ken ; Asami, Yukihiro ; Kakeya, Hideaki ; Osada, Hiroyuki. / Asymmetric total synthesis of (-)-azaspirene, a novel angiogenesis inhibitor. In: Journal of the American Chemical Society. 2002 ; Vol. 124, No. 41. pp. 12078-12079.
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AU - Mukaiyama, Takasuke

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