Total Syntheses of (+)-Valiolamine and (-)-1- epi-Valiolamine from Naturally Abundant (-)-Shikimic Acid.

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. [ABSTRACT FROM AUTHOR]