A concise and efficient synthesis of (-)-allosamizoline.
A regio- and stereocontrolled total synthesis of (-)-allosamizoline is described. The key steps for this synthesis are ring-closing metathesis to form the cyclopentene core, halocyclization to afford the oxazoline ring, and finally stereoselective alkene radical addition followed by an alkene isomerization reaction to install the hydroxymethyl group. (-)-Allosamizoline was prepared in a total of 13 steps and 22% overall yield.
Donohoe
Timothy J
TJ
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK. timothy.donohoe@chem.ox.ac.uk
Rosa
Carla P
CP
D003500:Cyclization; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013237:Stereoisomerism
C442377:allosamizoline; D005944:Glucosamine