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Communication | Regular issue | Vol 57, No. 5, 2002, pp.781-785
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9459
Enantioselective Synthesis of (-)-N-Boc-7-azabicyclo[2.2.1]heptan-2-one and (+)-N-Boc-4-amino-2-cyclohexen-1-one: Formal Total Synthesis of Both Enantiomers of Epibatidine

Toru Tachihara, Hiroyuki Watanabe, and Takeshi Kitahara*

*The University of Tokyo, Graduate School of Agricultural and Life Sciences, Department of Applied Biological Chemistry, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan

Abstract

we succeeded in the stereoselective synthesis of (—)-N-Boc-7- azabicyclo[2.2.1]heptan-2-one ((—)-2) and (+)-N-Boc-4-amino-2-cyclo- hexen-1-one ((+)-3), key intermediates to (—) and (+)-epibatidine from a common chiral building block ethyl (1R,2S)-5,5-ethylenedioxy-2- hydroxycyclohexanecarboxylate (4) . This constitutes the formal total synthesis of both enantiomers of epibatidine, a potent analgesic.