Related Experiment Videos
Synthesis of chiral pilocarpine analogues via a C-8 ketone intermediate
Kenneth G Holden1, Matthew N Mattson, Kyung Hoi Cha
1Holden Laboratories, 179 Mal Paso Road, Carmel, California 93923, and Department of Chemistry, University of California, Berkeley, California 94720, USA. KenHolden@aol.com
The Journal of Organic Chemistry
|August 17, 2002
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.