The total synthesis of (?-epi-mayol using a readily available geraniol as starting material is described. The stereospecific coupling of the two substituted geranyl units was achieved by the reaction of 8-hydroxy-geranial with 8-bromo-geranyl-phenyl-thioether in the presence of Cr(II) reagent. The resultant mixture was purified with flash chromatog. on SiO2 to give compound [I; R = b-OH, R1 = H] and its diastereoisomer I [R = a-OH, R1 = H] in 56% and 7% yield resp. I [R = b-H, R1 = H] was converted to tosyl ester I [R = a-OH, R1 = tosyl] and followed by ring closure in the presence of LDA gave compound II. The phenyl-thio group in II was cleaved by sodium-t-butanol to give the title compound (?-epi-mayol.

Key words: INFRARED SPECTROPHOTOMETRY, MASS SPECTROGRAPHY, NMR SPECTROMETRY, DITERPENES