A general method for making bicyclic compounds with nitrogen at a bridgehead--application to the halichlorine spiro subunit.
N-protected beta-amino aldehydes having the nitrogen in a ring are easily converted into Morita-Baylis-Hillman adducts; O-acetylation and N-deprotection result in spontaneous cyclization to bicyclic structures having nitrogen at a bridgehead.
Clive
Derrick L J
DL
Chemistry Department, University of Alberta, Edmonton, Alberta, Canada T6G 2G2. derrick.clive@ualberta.ca.
Yu
Maolin
M
Li
Zhiyong
Z
D000470:Alkaloids / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D008968:Molecular Conformation; D009584:Nitrogen / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D001643:Bridged Bicyclo Compounds; D013141:Spiro Compounds; C412666:halichlorine; D009584:Nitrogen