91318-97-7

Upstream product

• 32543-59-2 2-((1R,3S)-2,2-dimethyl-3-(2-oxopropyl)cyclopropyl)acetaldehyde 
• 91319-01-6 {(1S,3R)-2,2-Dimethyl-3-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopropyl}-acetic acid methyl ester 
• 91318-98-8 2,2-dimethyl-3-(2-tetrahydropyranyloxyethyl)-1-(2-oxopropyl)-cis-cyclopropane 
• 91318-95-5 2,2-dimethyl-3-(2-tetrahydropyranyloxyethyl)-1-(2-hydroxyethyl)-cis-cyclopropane 
• 82425-89-6 (-)-2-<(1R,3S)-2,2-Dimethyl-3-(2-oxopropyl)cyclopropyl>ethanol 
• 91318-96-6 2,2-dimethyl-1-(2-benzyloxyethyl)-3-(2-tetrahydropyranyloxyethyl)-cis-cyclopropane 

Downstream Products

• 91319-03-8 (+)-methyl-2,2-dimethyl-3-(2-benzyloxyethyl)-cyclopropane-cis-1-acetate 

Relevant academic research and scientific papers

Studies on the Terpenoids and Related Alicyclic Compounds. XXXII. A Synthesis of Chiral Dimethylcyclopropane Derivatives, Versatile Chiral Synthons for Casbane, Lathyrane, and Ingenane-Type Diterpenoids, from (+)-3-Carene

A synthesis of chiral dimethylcyclopropane derivatives, useful for the synthesis of casbane, lathyrane, and ingenane-type diterpenoids, from easily available (+)-3-carene is described.The silyl enol ether (8) was derived from (-)-cis-4-caranone (7b), which was obtained from (+)-3-carene (6).Ozonolysis of 8 gave 9a and 10.The right half segment (11b) for a synthesis of crotonitenone (3) was formed from 9a in three steps.The epoxide (12) was isomerized to a mixture of the allylic alcohols (13a) and (14a), which was transformed to the ketone (20) in five steps.Methylation of 20 followed by phosphorylation and reduction gave (+)-cis-4-caranone (23) in about 40 percent overall yield from 12.The methylester (+)-(32b) and its enantiomer (-)-(34b) were synthesized from (+)-6.Ozonolysis of a mixture of the silyl enol ether (30) and (31) followed by methylation with diazomethane gave 32a, which was hydrolyzed to give the desired (+)-32b.The enantiomer (-)-34b was derived from 32a in five steps.