(αR,4R,4aR,6aS,7R,8S,10R,11S)-Methyl α-acet-oxy-4-(3-furan-yl)- 10-hy-droxy-4a,7,9,9-tetra-methyl-2,13-dioxo-1,4,4a,5,6,6a,7,8,9,10,11, 12-dodeca-hydro-7,11-methano-2H-cyclo-octa-[f][2]benzopyran-8-acetate (6-O-acetyl-swietenolide) from the seeds of Swietenia macrophylla

Abstract

The mol-ecule of O-acetyl-swietenolide, C29H36O 9, isolated from the seeds of Swietenia macrophylla, features four six-membered rings connected together in the shape of a bowl; one of the inner rings adopts a twisted chair conformation owing to the C=C double bond. The furyl substitutent is connected to an outer ring, and it points away from the bowl cavity. The hy-droxy group is connected to a carbonyl O atom of an adjacent mol-ecule by an O - H⋯O hydrogen bond, generating a chain running along the b axis.