Absolute configuration of isoeichlerialactone

Abstract

The title seco-dammarane triterpenoid, C27H42O 4 (systematic name: 3-{(3S,3aR,5aR,6S,7S,9aR,9bR)-6,9a,9b-trimethyl- 3-[(R)-2-methyl-5-oxotetra-hydro-furan-2-yl]-7-(prop-1-en-2-yl) dodeca-hydro-1H-cyclo-penta-[a]naphthalen-6-yl}propanoic acid), has been isolated for the first time from the seeds of Aglaia forbesii. The mol-ecule has three fused rings and all rings are in trans-fused. The two cyclo-hexane rings are in standard chair conformations and the cyclo-pentane ring adopts an envelope conformation. Its absolute configuration was determined by the refinement of the Flack parameter to 0.26 (17). In the crystal, mol-ecules are linked into chains along [010] by O - H⋯O hydrogen bonds.