Synthesis of Acuminolide and 17-O-Acetylacuminolide from (+)-Sclareolide

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The synthesis of natural acuminolide and 17- O -acetylacuminolide is reported. Commerically available (+)-sclareolide was converted to epoxy alcohol 3, which upon acid-catalyzed cyclization afforded tricycle 14 . Reaction of 14 with 1 O 2 in the presence of a hindered base gave an inseparable mixture of acuminolide 1a and 16-epiacuminolide 1b in a 70:30 ratio. Chromatographic separation of the diacetates of 1a and 1b afforded pure 18a and 18b . An analogous reaction sequence was used in the synthesis of 17- O -acetylacuminolide ( 2a ) and 16- epi -17- O -acetylacuminolide ( 2b ).