Journal of the American Chemical Society p. 7008 - 7012 (1979)
Update date:2022-08-03
Topics:
Danishefsky
Harayama
Singh
The use of beta -phenylsulfinyl- alpha , beta -unsaturted carbonyl dieneophiles as synthetic equivalents of alpha , beta -ethynyl carbonyl systems has been demonstrated. The sulfoxides were prepared by oxidation of the sulfides, which in turn were obtained from the beta -dicarbonyl systems by standard methods. A key feature of the scheme is that the phenylsulfinyl group does not compete with the carbonyl function in determining the regiochemistry of cycloaddition with the highly nucleophilic trans-1-methoxy-3-trimethylsilyloxy-1,3-butadiene. Application of the methodology to the synthesis of the disodium prephenate dimethyl acetals is described.
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Doi:10.1007/BF00910977
(1979)Doi:10.1021/om030487v
(2004)Doi:10.1093/pa/53.4.657
(1937)Doi:10.1021/ie50373a012
(1941)Doi:10.1002/mrc.1260330509
(1995)Doi:10.1021/om010773b
(2002)
