109122-52-3Relevant academic research and scientific papers
Prins Reaction of 2-Oxabicyclooct-6-en-3-one and Related Derivatives
Toemoeskoezi, Istvan,Gruber, Lajos,Baitz-Gacs, Eszter
, p. 10345 - 10352 (2007/10/02)
Reaction of formaldehyde with the title olefinic lactone in acetic acid affords diacetate of 1,3-diol (2a) as the main product in 50-60percent yield via regioselective trans-addition.Less favourable results were obtained with related bicyclic derivatives.
BF3-MEDIATED REACTION OF A SULPHONE WITH ALDEHYDES. A METHOD FOR STEREOSPECIFIC CONSTRUCTION OF PROSTAGLANDIN ω-CHAIN
Achmatowicz, B.,Baranowska, E.,Daniewski, A. R.,Pankowski, J.,Wicha, J.
, p. 4989 - 4998 (2007/10/02)
A new method for stereospecific construction of the allylic alcohol moiety of prostaglandins, based on application of optically active α-hydroxy aldehydes, is described.In the presence of BF3*Et2O, lithiated sulphones 1 prepared from Corey aldehyde, and carbonyl compounds 2 give the corresponding adducts 3 in moderate to excellent yields, while in the absence of the Lewis acid either no products or only their traces were formed.The addition products 3, in the form of benzoates, mesylates or free alcohols, were subjected to reductive elimination by means of sodium amalgam to give the alkenes 4.Compounds 4d and 4f were transformed into racemic and natural PGF2α, respectively, in line with the known method.
