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Synthesis of (±)-cis-Calamenene;

Parimi Atchuta Ramaiah, A. S. RAO

Abstract

Hydroboration of 4 furnishes a mixture of primary alcohols 5 and 6. The stereochemistry of the crystalline half ester 7 has been established by X-ray studies. While the oxidation of 5 with Jones reagent furnishes the aldehyde 9 in low yield due to the formation of the by product 3, oxidation with Moffatt reagent furnishes the aldehyde 9 in satisfactory yields. cis-Calamenene 1 has been prepared from 9.

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Key concepts: Chemistry, Reagent, Aldehyde, Hydroboration, Yield (engineering), Organic chemistry, Primary (astronomy), Medicinal chemistry