Enantioselective total synthesis of macrolide antitumor agent (-)-lasonolide A.
[structure: see text] An enantioselective total synthesis of (-)-lasonolide A is described. The upper tetrahydropyran ring was constructed stereoselectively by an intramolecular 1,3-dipolar cycloaddition reaction. The bicyclic isooxazoline led to the tetrahydropyran ring as well as the quaternary stereocenter present in the molecule. The lower tetrahydropyran ring was assembled by a catalytic asymmetric hetero-Diels-Alder reaction as the key step. Three stereocenters were enantioselectively installed in this single step reaction.
Ghosh
Arun K
AK
Departments of Chemistry and Medicinal Chemistry, Purdue University, West Lafayette, Indiana 47907, USA. akghosh@purdue.edu
Gong
Gangli
G
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010091:Oximes / Q000737:chemistry; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D018942:Macrolides; D010091:Oximes; C450700:lasonolide A