Synthesis of chiral pilocarpine analogues via a C-8 ketone intermediate.
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.
Holden Laboratories, 179 Mal Paso Road, Carmel, California 93923, and Department of Chemistry, University of California, Berkeley, California 94720, USA. KenHolden@aol.com
Kenneth G
KG
Holden
Matthew N
MN
Mattson
Kyung Hoi
KH
Cha
Henry
H
Rapoport
D002851:Chromatography, High Pressure Liquid; D007093:Imidazoles / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry; D013058:Mass Spectrometry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010862:Pilocarpine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D007093:Imidazoles; D007659:Ketones; D007783:Lactones; D010862:Pilocarpine