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Studies toward Total Synthesis of (±)-Caldaphnidine C via One-Pot Sequential Intramolecular Vilsmeier-Haack and
Jonathan Boudreault1, François Lévesque1, Guillaume Bélanger1
1Département de Chimie, Université de Sherbrooke , 2500 boulevard Université, Sherbrooke, Québec, J1K 2R1, Canada.
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.
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