title: Studies toward Total Synthesis of (±)-Caldaphnidine C via One-Pot Sequential Intramolecular Vilsmeier-Haack and Azomethine Ylide 1,3-Dipolar Cycloaddition.
abstract: An application of a one-pot sequential Vilsmeier-Haack cyclization and intramolecular azomethine ylide 1,3-dipolar cycloaddition toward the total synthesis of (±)-caldaphnidine C is presented. It allowed an efficient formation of three cycles with perfect control of four of the five newly created stereogenic centers including one all-carbon quaternary center. Two synthetic strategies to produce the key-step precursor, the investigation and optimization of the cyclization partners (nucleophile, azomethine ylide, and dipolarophile), and further derivatization of the cycloadduct are reported.
authors.affiliation: Département de Chimie, Université de Sherbrooke , 2500 boulevard Université, Sherbrooke, Québec, J1K 2R1, Canada.
authors.forename: Jonathan
authors.initials: J
authors.lastname: Boudreault
authors.affiliation: Département de Chimie, Université de Sherbrooke , 2500 boulevard Université, Sherbrooke, Québec, J1K 2R1, Canada.
authors.forename: François
authors.initials: F
authors.lastname: Lévesque
authors.affiliation: Département de Chimie, Université de Sherbrooke , 2500 boulevard Université, Sherbrooke, Québec, J1K 2R1, Canada.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Bélanger