Synthesis of chiral pilocarpine analogues via a C-8 ketone intermediate

…, MN Mattson, KH Cha, H Rapoport

Index: Holden, Kenneth G; Mattson, Matthew N; Cha, Kyung Hoi; Rapoport, Henry The Journal of organic chemistry, 2002 , vol. 67, # 17 p. 5913 - 5918

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Citation Number: 27

Abstract

The synthesis of a chiral pilocarpine analogue 3 in which the lactone ring is replaced by an oxazolidinone and the bridging methylene group is in the ketone oxidation state has been accomplished. The utility of this compound as a key intermediate for the preparation of more complex structures was demonstrated by its reduction to two alcohol epimers and its reaction with a methylene ylide.