title: Synthesis of the stenine ring system from pyrrole.
abstract: The skeleton of the stemona alkaloid, stenine, has been synthesized starting from pyrrole, employing an asymmetric organocatalyzed cyclization, Sonogashira coupling, a diastereoselective intramolecular propargylic Barbier reaction, cyclocarbonylation, and diastereoselective alkene reduction. Modulation of the electron-rich nature of the pyrrole nucleus by employing an α-trifluoroacetyl group is essential. The α-trifluoroacetyl group may be rapidly removed under carefully defined, mild conditions.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371. roderick@ntu.edu.sg
authors.forename: Roderick W
authors.initials: RW
authors.lastname: Bates
authors.forename: S
authors.initials: S
authors.lastname: Sridhar
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D006868:Hydrolysis; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D011758:Pyrroles; C441784:stenine