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Catalytic asymmetric synthesis of 19,20-dihydroakuammicine

✍ Scribed by Ken Ohori; Satoshi Shimizu; Takashi Ohshima; Masakatsu Shibasaki

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 116 KB
Volume: 12
Category: Article
ISSN: 0899-0042
DOI: 10.1002/(sici)1520-636x(2000)12:5/6<400::aid-chir18>3.0.co;2-h

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✦ Synopsis

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.

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