title: Concise synthesis of alkaloid (-)-205B.
abstract: Described herein is a short total synthesis of alkaloid (-)-205B (1) by means of an anti-selective SN2' alkylation of an attractively functionalized cyclopropanol and diastereoselective cyclization of the resulting aminoallene adduct for bicyclic ring formation. The synthesis features a general route to cis- or trans-2,6-disubstituted piperidines by lithium aluminum hydride reduction of the imine intermediate by an appropriate choice of solvent and cis- or trans-2,5-disubstituted pyrrolidines by an exceptional level of chirality transfer from a pendant allene. Particularly noteworthy are the brevity and convergence made possible by a segment-coupling strategy.
authors: Department of Chemistry, Wayne State University , 5101 Cass Avenue, Detroit, Michigan 48202, United States.
authors: Nagavaram Narsimha
authors: NN
authors: Rao
authors: Jin Kun
authors: JK
authors: Cha
mesh_terms: D000470:Alkaloids / Q000096:biosynthesis*; D003500:Cyclization
chemical_list: D000470:Alkaloids