Asymmetric total synthesis of pseurotin A

Yujiro Hayashi, Mitsuru Shoji, Shinpei Yamaguchi, Takasuke Mukaiyama, Junichiro Yamaguchi, Hideaki Kakeya, Hiroyuki Osada

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

(Matrix presented) The asymmetric total syntheses of pseurotin A and 8-O-demethylpseurotin A have been accomplished. Key reactions are a NaH-promoted intramolecular cyclization of an alkynylamide to form a γ-lactam, an aldol reaction of a benzylidene-substituted ketone, and the late-stage introduction of the benzoyl group by a selective oxidation of a benzylidene moiety with dimethyldioxirane (DMD).

Original languageEnglish
Pages (from-to)2287-2290
Number of pages4
JournalOrganic Letters
Volume5
Issue number13
DOIs
Publication statusPublished - 2003 Jun 26
Externally publishedYes

Fingerprint

Lactams
Cyclization
Ketones
Oxidation
synthesis
ketones
oxidation
matrices
pseurotin
dimethyldioxirane
3-hydroxybutanal

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Hayashi, Y., Shoji, M., Yamaguchi, S., Mukaiyama, T., Yamaguchi, J., Kakeya, H., & Osada, H. (2003). Asymmetric total synthesis of pseurotin A. Organic Letters, 5(13), 2287-2290. https://doi.org/10.1021/ol034630s

Asymmetric total synthesis of pseurotin A. / Hayashi, Yujiro; Shoji, Mitsuru; Yamaguchi, Shinpei; Mukaiyama, Takasuke; Yamaguchi, Junichiro; Kakeya, Hideaki; Osada, Hiroyuki.

In: Organic Letters, Vol. 5, No. 13, 26.06.2003, p. 2287-2290.

Research output: Contribution to journalArticle

Hayashi, Y, Shoji, M, Yamaguchi, S, Mukaiyama, T, Yamaguchi, J, Kakeya, H & Osada, H 2003, 'Asymmetric total synthesis of pseurotin A', Organic Letters, vol. 5, no. 13, pp. 2287-2290. https://doi.org/10.1021/ol034630s
Hayashi Y, Shoji M, Yamaguchi S, Mukaiyama T, Yamaguchi J, Kakeya H et al. Asymmetric total synthesis of pseurotin A. Organic Letters. 2003 Jun 26;5(13):2287-2290. https://doi.org/10.1021/ol034630s
Hayashi, Yujiro ; Shoji, Mitsuru ; Yamaguchi, Shinpei ; Mukaiyama, Takasuke ; Yamaguchi, Junichiro ; Kakeya, Hideaki ; Osada, Hiroyuki. / Asymmetric total synthesis of pseurotin A. In: Organic Letters. 2003 ; Vol. 5, No. 13. pp. 2287-2290.
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