Short synthesis of (+)-aspicillin via asymmetric hexahydroxylation of a triene

Article abstract of DOI:10.1021/jo00084a006

Asymmetric synthesis of the 18-membered lichen macrolide (+)-aspicilin has been achieved in 14 steps and 11% overall yield, starting from an achiral hydrocarbon, (3E)-hexadeca-1,3,15-triene. All four stereogenic carbinol centers have been introduced by three Sharpless asymmetric dihydroxylation (AD) reactions, using both AD-mix-β and AD-mix-α to produce the hexol with very high regio- and enantioselectivity (epimeric excess of 88% at position 2, 96% at positions 3 and 4, and 86% at position 15).