35 Epoxide基を持つ光学活性Terpene類の合成

抄録

We developed new general synthetic routes for optically active epoxyterpenes from an optically active α-amino acid without a resolution step. The keto acetonide(8), a key intermediate for these syntheses, was synthesized from L-glutamic acid and converted to R-(+)-epoxygeraniol(14), R-(+)-, S-(-)-marmin(17) and R-(+)-epoxyaurapten(18). Naturally occurring (+)-marmin and (+)-epoxyaurapten were shown to possess R-configuration. Further, optically pure R-(+)-epoxyfarnesol(19) and R-(+)-, S-(-)-squalene-2,3-oxide(45) were synthesized.