title: Enantioselective total synthesis of (-)-zampanolide, a potent microtubule-stabilizing agent.
abstract: An enantioselective total synthesis of zampanolide has been accomplished using a novel DDQ/Brønsted acid promoted cyclization as the key reaction. The synthesis features cross-metathesis to construct the trisubstituted olefin and a ring-closing metathesis to form the macrolactone. The final N-acyl aminal formation was stereoselectively accomplished by an organocatalytic reaction.
authors: Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, USA. akghosh@purdue.edu
authors: Arun K
authors: AK
authors: Ghosh
authors: Xu
authors: X
authors: Cheng
mesh_terms: D003500:Cyclization; D005079:Excipients / Q000138:chemical synthesis*; D018942:Macrolides / Q000138:chemical synthesis*; D008870:Microtubules / Q000378:metabolism; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D005079:Excipients; D018942:Macrolides; C444900:zampanolide