Catalytic asymmetric synthesis of 19,20-dihydroakuammicine

Ken Ohori, Satoshi Shimizu, Takashi Ohshima, Masakatsu Shibasaki

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

An enantiocontrolled total synthesis of 19,20-dihydroakuammicine using a catalytic asymmetric MiChael addition of dimethyl malonate to cyclohexenone as the key step is described. The above catalytic asymmetric Michael addition proceeds quite efficiently in the presence of a heterobimetalic asymmetric catalyst (ALB-KO-t-Bu-MS 4A, 0.3 mol%), giving the corresponding Michael adduct in 94% yield and 99% ee. (C) 2000 Wiley-Liss, Inc.

Original languageEnglish
Pages (from-to)400-403
Number of pages4
JournalChirality
Volume12
Issue number5-6
Publication statusPublished - Jan 1 2000
Externally publishedYes

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Catalysts
19,20-dihydroakuammicine
methyl malonate

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

Cite this

Ohori, K., Shimizu, S., Ohshima, T., & Shibasaki, M. (2000). Catalytic asymmetric synthesis of 19,20-dihydroakuammicine. Chirality, 12(5-6), 400-403.

Catalytic asymmetric synthesis of 19,20-dihydroakuammicine. / Ohori, Ken; Shimizu, Satoshi; Ohshima, Takashi; Shibasaki, Masakatsu.

In: Chirality, Vol. 12, No. 5-6, 01.01.2000, p. 400-403.

Research output: Contribution to journalArticle

Ohori, K, Shimizu, S, Ohshima, T & Shibasaki, M 2000, 'Catalytic asymmetric synthesis of 19,20-dihydroakuammicine', Chirality, vol. 12, no. 5-6, pp. 400-403.
Ohori K, Shimizu S, Ohshima T, Shibasaki M. Catalytic asymmetric synthesis of 19,20-dihydroakuammicine. Chirality. 2000 Jan 1;12(5-6):400-403.
Ohori, Ken ; Shimizu, Satoshi ; Ohshima, Takashi ; Shibasaki, Masakatsu. / Catalytic asymmetric synthesis of 19,20-dihydroakuammicine. In: Chirality. 2000 ; Vol. 12, No. 5-6. pp. 400-403.
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