51864-98-3Relevant academic research and scientific papers
Palladium(0)-catalysed conversion of α-acetylenic epoxides into α-allenic alcohols. Novel route to (+/-)-2,3-octadiene-5,7-diyn-1-ol, a metabolite from fungus Cortinellus berkeleyanus
Kleijn, H.,Meijer, J.,Overbeek, G. C.,Vermeer. P.
, p. 97 - 101 (2007/10/02)
α-Acetylenic epoxides, (1), have been converted into α-allenic alcohols, RR'C=C=CR"-CH2OH (3), by means of a palladium(0)-promoted reaction with R-ZnCl (2; R: Me3Si(CC)n- (n = 1 or 2), H2C=CH- or t-BuCH=C=CH-).Using this method, an improved synthesis of (+/-)-2,3-octadiene-5,7-diyn-1-ol, a metabolite from fungus Cortinellus berkeleyanus, has been developed.The method is not suited to the preparation of α-allenic alcohols from 1 and, for example, BuZnCl because of substantial formation of reduction products, HCR'=C=CR"-CH2OH.For the preparation of 3 from R = Me3SiCC other acetylides Me3SiCC-M were also studied, viz.M = Li, MgCl, Cu or Cu1/2Li1/2 but only with the cuprate could a reasonable conversion of 1 be realized.
