An 18-Chloro-4α-hydroxy Derivative of 19-Acetylteupolin IV: a Neo-clerodane Diterpenoid of Biological Interest

The title compound, (12S)-7β,19-diacetoxy-18-chloro-15,16-epoxy-4α-hydroxy-6-oxo-neo- cleroda-13(16),14-dien-20,12-olide [systematic name: 4′a-(acetoxymethyl)-5′-(chloromethyl)-5′-hydroxy-5-(3-furyl)-5′- hydroxy-2′-methyl-2,4′-dioxodecahydrospiro[furan-3(2H),1′(2′H)naphthalen]- 3′-yl acetate; C₂₄H₂₉ClO₉}, is of interest on account of its biological activity as an insect antifeedant. The fused six-membered rings of the molecule show similar chair conformations. The crystal contains dimeric molecules, formed via bifurcated (intra- and intermolecular) O-H...O hydrogen bonds.

-1