Tetrahedron p. 4989 - 4998 (1988)
Update date:2022-08-05
Topics:
Achmatowicz, B.
Baranowska, E.
Daniewski, A. R.
Pankowski, J.
Wicha, J.
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.
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Doi:10.1021/om00095a006
(1988)Doi:10.1016/S0960-894X(03)00393-7
(2003)Doi:10.1016/j.ejmech.2016.04.017
(2016)Doi:10.1021/ol802794t
(2009)Doi:10.1016/S0040-4039(01)91161-X
(1984)Doi:10.1021/jm034015u
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