Catalytic asymmetric synthesis of 19,20-dihydroakuammicine

Ken Ohori; Satoshi Shimizu; Takashi Ohshima; Masakatsu Shibasaki

doi:10.1002/(sici)1520-636x(2000)12:5/6<400::aid-chir18>3.0.co;2-h

Catalytic asymmetric synthesis of 19,20-dihydroakuammicine

Ken Ohori, Satoshi Shimizu, Takashi Ohshima, Masakatsu Shibasaki

Research output: Contribution to journal › Article › peer-review

20 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 language	English
Pages (from-to)	400-403
Number of pages	4
Journal	Chirality
Volume	12
Issue number	5-6
DOIs	https://doi.org/10.1002/(sici)1520-636x(2000)12:5/6<400::aid-chir18>3.0.co;2-h
Publication status	Published - Jan 1 2000
Externally published	Yes

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Catalysis
Pharmacology
Drug Discovery
Spectroscopy
Organic Chemistry

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10.1002/(sici)1520-636x(2000)12:5/6<400::aid-chir18>3.0.co;2-h

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T1 - Catalytic asymmetric synthesis of 19,20-dihydroakuammicine

AU - Ohori, Ken

AU - Shimizu, Satoshi

AU - Ohshima, Takashi

AU - Shibasaki, Masakatsu

PY - 2000/1/1

Y1 - 2000/1/1

N2 - 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.

AB - 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.

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ER -

Catalytic asymmetric synthesis of 19,20-dihydroakuammicine

Abstract

All Science Journal Classification (ASJC) codes

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