Chiral Synthesis of Furanosesquiterpene, (+)-Ipomeamarone

Abstract

+)-Ipomeamarone, a furh~ses~uiterpene isolated from mold-damaged sweet potato (Ipomea batatas) as one of the phytoalexins, was synthesized starting from (S)-lactic acid as the c h i d source using Seehach's chiral selfreproduction method.(+)-Ipomeamarone ( 1) is a furanosesquiterpene isolated from the mold-damaged sweet potato Ipomea batatas as one of the first phytoalexins.lThe structure of ipomeamarone (1) was elucidated by Kubota et 01.2 and then its absolute stereochemistry was determined by Nakanishi et a1.3 in 1983.Interestingly, the (-)-enantiomer of (+)-ipomeamarone (1) was also found in nature, and its name is (-)-ngaione (2).which was isolated from Myoporum deserti4