Stereoselektive Synthese von 3,5‐disubstituierten Octahydroindolizinen

Abstract

Abstract A Stereoselective Synthesis of 3,5‐Disubstituted Octahydroindolizines On catalytic hydrogenation, methyl 6‐nitro‐9‐oxodecanoate (1) underwent cyclization to 2 which, after hydrolysis, gave the bicyclic product 4 . By another series of reactions, 2 was transformed to methyl 3‐methyloctahydroindolizine‐5‐carboxylate ( 7 ), Conversions of 7a to its C(5)‐epimer 7b and vice versa were accomplished and the configurations of 7a and 7b determined. Finally, 7b was reduced in three steps to 11 (overall yield from 1 , 24%), which is an analog of several natural products.