levorotatory and dextrorotatory 6, 10-Dimethylbicyclo [5.3.0] decan-3-ones (IIIa and IIIb) were derived from guaiol (I), and the former was converted into dexitrorotatory 6, 10-dimethylbicyclo [5.3.0] decan-4-one (XI).
Guaioxide is a saturated sesquiterpene oxide, for which four possible structures have been suggested. Attempted microbial hydroxylation of the compound was successful, this led to a way to open its oxide linkage under mild conditions, and to a decision of the stereochemistry II for guaioxide.