Synthesis of (4 R,15 R,16 R,21 S)- and (4 R,15 S,16 S,21 S)-rollicosin

Abstract

A convergent synthesis of (4 R,15 R,16 R,21 S)-rollicosin ( 1 ) and (4 R,15 S,16 S,21 S)-rollicosin ( 2 ) was accomplished. Hydroxy lactone 6a and/or 6b were synthesized from 4-pentyn-1-ol, and α,β-unsaturated lactone 7 was synthesized from γ-lactone 8 and 5-hexen-1-ol. Inhibitory activity of these compounds was examined with bovine heart mitochondrial complex I.