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Communication | Regular issue | Vol 38, No. 9, 1994, pp.1961-1964
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6803
A New Procedure for Construction of 2,6-trans-Disubstituted Piperidines Using Osmium-catalyzed Asymmetric Dihydroxylation: Application to the Synthesis of (+)-Epidihydropinidine and (+)-Solenopsin A1

Hiroki Takahata,* Kumiko Inose, Naomi Araya, and Takefumi Momose*

*Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama, Toyama 930-0194, Japan

Abstract

An aymmetric synthesis of (+)-epidihydropinidine (1) and (+)-solenopsin A (2) has been achieved by starting with the Sharpless asymmetric dihydroxylation of the α-amino acid-derived N-alkenylurethanes (3) followed by subsequent aminocyclization.