Synthesis of (+)-Juvabione, a Compound with Juvenile Hormone Activity

(+)-Juvabione 1 was synthesized by employing (1R,4S,6S)-6-hydroxybicyclo[2.2.2]octan-2-one 2 as a chiral source. (+)-Juvabione 1 shows juvenile hormone activity, and its racemate has been repeatedly synthesized.1) Optically active 1 was synthesized by Pawson et al. from (+)-limonene, 2) and by Trost et al. from (+)-perillaldehyde.3) However, their syntheses were not at all efficient for providing a suitable amount of optically active 1.