Use of aziridines for the stereocontrolled synthesis of (-)-LL-C10037α, (+)-MT35214, and (+)-4-epi-MT35214.
Strategies for the synthesis of the title compounds have been developed using a diastereoselective aziridination reaction of 4-O-substituted cyclohexenones. Aziridination using a chiral amine permitted resolution of a 4-hydroxycyclohexane derivative, and this resulted in the synthesis of both enantiomers of the title compound. Alternatively, the chiral 4-hydroxycyclohexenone starting material was derived from quinic acid. In both cases stereoselective epoxidation and opening of the aziridine ring with hydrazoic acid afforded the 2-azidocyclohexenone, which was transformed to the 2-acetamido group present in the natural product.
Instituto de Tecnologia Quı́mica e Biológica, Universidade Nova de Lisboa , Av. da República, 2780-157 Oeiras, Portugal.
Christopher D
CD
Maycock
Paula
P
Rodrigues
M Rita
MR
Ventura
D000081:Acetamides / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry*; D011809:Quinones / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
C000592555:4-epi-MT35214; C548047:4-hydroxycyclohexenone; D000081:Acetamides; D001388:Aziridines; D003512:Cyclohexanones; D011809:Quinones; C033132:aziridine; C043671:LL-C 10037alpha