339157-74-3Relevant academic research and scientific papers
Synthesis of (-)-erythrodiene and (+)-7-epispirojatamol via intramolecular Pd-catalyzed allylzincation
Oppolzer, Wolfgang,Flachsmann, Felix
, p. 416 - 430 (2007/10/03)
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.
