Use of 1,1'-binaphthalene-8,8'-diol as a chiral auxiliary for asymmetric Michael addition. Application to the syntheses of turmeronol A and B

DOI: 10.1248/cpb.47.1053

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1053 - 1055 (1999)

Update date:2022-07-30

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Authors:

Tanaka, Kiyoshi

Nuruzzaman, Mohammad

Yoshida, Masato

Asakawa, Naoyuki

Yang, Xiao-Shen

Tsubaki, Kazunori

Fuji, Kaoru

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Article abstract of DOI:10.1248/cpb.47.1053

Highly diastereoselective Michael addition of lithium diorganocuprates to the half-ester of 1,1'-binaphthalene-8,8'-diol gave β-substituted esters with high enantiomeric excess after methanolysis. The optically active phenolic sesquiterpenes turmeronol A (1) and B (2) have been synthesized using this reaction as a key step.

Full text of DOI:10.1248/cpb.47.1053

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