339157-70-9

Upstream product

• 339157-71-0 (1R,5R)-5-isopropyl-2-methylidene-1-(pent-4-enyl)cyclohexanol 
• 339267-31-1 (5R)-5-isopropyl-2-methylene cyclohexanol 
• 93215-97-5 (5R)-2-methylidene-5-isopropylcyclohexanone 
• 1195-31-9 (+)-p-menth-1-ene 
• 339157-72-1 (R)-1-Chloromethyl-4-isopropyl-2-pent-4-enyl-cyclohexene 
• 339157-69-6 (1R,5R)-5-isopropyl-2-methylidene-1-(pent-4-enyl)cyclohexyl acetate 

Relevant academic research and scientific papers

Synthesis of (-)-erythrodiene and (+)-7-epispirojatamol via intramolecular Pd-catalyzed allylzincation

Two spirobicyclic sesquiterpenoids, (-)-erythrodiene (1) and (+)-7-epispirojatamol (30), were synthesized in enantiomericaliy pure form via an intramolecular allylzincation process. The allylzinc species were formed in the presence of Et2Zn via transmetallation of a catalytically generated allylpalladium intermediate. Several Pd catalysts were tested for this transformation, and [Pd(OAc)2]/Bu3P (1 equiv.) was found to be, by far, the most effective. Whereas the preparation of 1 involved allylzincation of a tethered terminal olefin, 30 was formed via a novel intramolecular allyl zincation of a methyl ketone. Both reactions showed the same stereochemical preference, yielding the spirobicyclic products in 95:5 and 4:1 diastereoisomer ratios, respectively.