Total Syntheses of (+)‐Valiolamine and (–)‐1‐<i>epi</i>‐Valiolamine from Naturally Abundant (–)‐Shikimic Acid

Abstract

Abstract Total syntheses of (+)‐valiolamine ( 1 ) and (–)‐1‐ epi ‐valiolamine ( 2 ) from the naturally abundant (–)‐shikimic acid are described. Ethyl 3‐ epi ‐5‐ O ‐methylsulfonyl‐shikimate ( 3 ), as the key common intermediate, was first synthesized in five steps in 74 % overall yield, and then converted into the targets 1 and 2 in seven steps in 48 and 41 % overall yield, respectively.