A Stereocontrolled Synthesis of the Pheromone 4-Methyl-3-heptanol : Novel and Selective CC-Linking Reactions

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)]


Published in:
Angewandte Chemie, International Edition, 21, 309-310
Year:
1982
Keywords:
Note:
CAN 97:55517 26-2 Biomolecules and Their Synthetic Analogs Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz. Journal 0044-8249 written in German. 367-46-4 Role: RCT (Reactant), RACT (Reactant or reagent) (condensation reaction of, with butenylpotassium); 590-18-1 Role: PROC (Process) (conversion of, to potassium deriv.); 624-64-6 Role: PROC (Process) (conversion of, to potassium salt and isomerization of); 73891-67-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and condensation reaction of, with fluorodimethoxyborane); 83791-55-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydrogenation of); 76347-11-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and stereoselective addn. reaction of, with propanal); 1538-21-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and stereoselective homologation of, with trimethylaluminum); 1589-07-7P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 63707-89-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, via stereoselective alkylation of propanal with buteneboronate); 123-38-6 Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective addn. reaction of, with di-Me buteneboronate)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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