Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 43, No. 5, 1996, pp.1031-1047
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7421
■ Asymmetric Synthesis of Benzylic Quaternary Carbon Center via an Enzymatic Reaction

Shunsaku Shiotani,* Hirohiko Okada, Kumiko Nakamata, Takako Yamamoto, and Fumie Sekino

*Department of Chemistry, Faculty of Science, Toyama University, Gofuku 3190, Toyama 930, Japan

Abstract

(R)-(+)-((R)-(+)-12) and (S)-(-)-1-formyl-1-methyl-7-methoxy-1,2,3,4-tetrahydronaphthalene ((S)-(-)-12) were synthesized based on enantioselective PLE hydrolysis of diethyl 2-(m-methoxyphenyl)-2-methylmalonate. From (R)-(+)-12, (+)-O-Methylaphanorphine (16) and (-)-aphanorphine were synthesized. (S)-(+)-1-(N-Acetyl-N-methylaminoethyl)-1-methyl-7-methoxytetralin (25) was synthesized from (S)-(-)-12. This transformation constitutes a formal synthesis of (-)-eptazocine.