Synthesis of optically pure forms of ipsenol
AssigneeAldrich Chemical Company, Inc.
InventorHerbert C. Brown
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Abstract
An improved process for preparing either optically pure enantiomer of the bark beetle pheromones ipsenol and ipsdienol is provided. The process is also applicable to the condensation of aldehydes of widely varying properties to the corresponding chiral alcohol.
Claims12
An improved process for producing diterpenyl-(2'-isoprenyl)boranes comprising the steps of reacting isoprenylpotassium with a compound of the formula (terpenyl).sub.2 BX at a temperature of from room temperature to -100.degree. C. wherein terpenyl is selected from the group consisting of .sup.d isopinocampheyl, .sup.l isopinocampheyl, 2-isocaranyl and 4-isocaranyl;
- B is boron;
- and wherein X is alkoxy or halo.
An improved process for the chiral isoprenylation of aldehydes comprising reacting a desired aldehyde with a diterpenyl-(2'-isoprenyl)borane.
An improved process for synthesizing both optical isomers of ipsenol comprising treating isovaleraldehyde with a compound selected from the group consisting of .sup.d diterpenyl-B-(2'-isoprenyl) and .sup.l diterpenyl-B-(2'-isoprenyl).
Dependencies are inferred from the claim text.