Site-Selective Hydrosilylation of Botryococcene - The Algal Biomass Hydrocarbon Oil

摘要

An algal acyclic triterpene botryococcene ((E)- 2,3,7,10,13,16,20,21-octamethyl-6,17-dimethylene-10-vinyldocosa- 1,11,21-triene), new biomass for material sources, which has three-types of six carbon-carbon double bonds, i. e., four vinylidenes at C2,6,17,21-positions, one C10-vinyl, and one C11- 12 internal olefin, in the molecule underwent hydrosilylation of various organosilanes in the presence of Pt(0) 1,3-divinyl- 1,1,3,3-tetramethyldisiloxane complex (Karstedt's catalyst). Various hydrosilylated botryococcene derivatives were site- and regioselectively obtained in high yields by an anti-Markovnikov type addition at the C10-vinyl moiety without any isomerizations of the unsaturated triterpenoid skeleton.