An expedient total synthesis of (±)-caparratriene

Article abstract of DOI:10.1016/S0040-4039(99)00865-5

(±)-Caparratriene has been synthesized by two succinct routes. The first relies on two Wittig reactions and produces (±)-caparratriene and its 2Z isomer as an inseparable 2:1 mixture. The second more efficient synthesis produces only the naturally occurring 2E isomer and proceeds in 36% overall yield. The key step in this short synthesis is the Suzuki coupling of E-2- bromo-2-butene with the E-vinyl borane derived from 4,8-dimethyl-7-nonen-1- yne.