title: Total synthesis of (-)-calyciphylline N.
abstract: The total synthesis of the architecturally complex Daphniphyllum alkaloid (-)-calyciphylline N has been achieved. Highlights of the synthesis include a Et2AlCl-promoted, highly stereoselective, susbtrate-controlled intramolecular Diels-Alder reaction, a transannular enolate alkylation, an effective Stille carbonylation/Nazarov cyclization sequence, and a high-risk diastereoselective hydrogenation of a fully substituted conjugated diene ester.
authors: Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania , Philadelphia, Pennsylvania 19104, United States.
authors: Artem
authors: A
authors: Shvartsbart
authors: Amos B
authors: AB
authors: Smith
mesh_terms: D060326:Chemistry Techniques, Synthetic; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D011083:Polycyclic Compounds; C535098:calyciphylline N