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2005
Hormones
U 1000
34- 270
Solvolysis of Allylic Prostaglandin Mesylates: Moderate 1,3-syn-Stereoselectivity.
— The substitution reaction of mesylates of prostaglandin alcohols like (I) is studied.
A mixture of epimeric substitution products [cf. (III)/(IV)] as well as their allylic rearrangement products [cf. (V)/(VI)] is obtained in this reaction. The influence of a variety
of factors on the regio- and stereoselectivity is studied. It includes structure and configuration of the starting alcohol, the reaction temperature, and the nature of thenucleophile. The reaction mechanism is discussed. — (LAPITSKAYA, M. A.; DEMIN, P.
M.; ZATONSKY, G. V.; PIVNITSKY*, K. K.; Russ. Chem. Bull. 53 (2004) 11,
2617-2625; Zelinsky Inst. Org. Chem., Russ. Acad. Sci., Moscow 117913, Russia;
Eng.) — Mischke
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