1, 6-Dihydro-3 (2H)-pyridinones. VIII. Total Synthesis of (±)-Corynantheidol and Formal Synthesis of (±)-Quinine

Abstract

cis-3, 4-Disubstituted piperidine compounds (2 and 3) were stereoselectively prepared from benzyl 3-(1, 3-dioxolan-2-ylmethyl)-1, 2, 3, 6-tetrahydropyridine-1-carboxylate (13) via the ketone (17). A total synthesis of (±)-corynantheidol (4) and a formal synthesis of (±)-quinine (5) have also been achieved from the piperidines 2 and 3, respectively.