Abstract

The Scolytus multistriatus aggregation pheromone (S,S)-4-methyl-3-heptanol was prepd. via 2 stereoselective steps. Reaction of (Z)-2-butenyl potassium with FB(OMe)2 at -75 Deg gave (Z)-MeCH:CHCH2B(OMe)2 which reacted with EtCHO to give >60% 96:4 erythro-4-methyl-5-hexene-3-ol (I) and threo-4-methyl-5-hexen-3-ol. Stereoselective homologation of I with AlMe3-TiCl4 and subsequent hydrolysis gave 32% II (RR = bond). This was hydrogenated to give quant. II (R = H). [on SciFinder (R)]

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