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2005
Steroids
U 0300
27- 184
Nucleosteroids: Synthesis of Purinyl-Steroid Derivatives under Mitsunobu Reaction Conditions. — To broaden the range of steroids, potentially useful as starting materials for coupling with nitrogenated bases, the feasibility of the conditions of the Mitsunobu reaction, applied to the particular case of coupling cholesterol (I) with chloropurine (II) is studied. Three principal products are obtained: cholestene stereoisomers
(III) and (IV), and 3,5-cyclocholestane (V). Formation of a homoallylic carbocation
through participation of the double bond of (I) may be responsible for the stereochemical and structural diversity of the coupling products. — (CADENAS, R. A.; GELPI*,
M. E.; MOSETTIG, J.; J. Heterocycl. Chem. 42 (2005) 1, 1-3; Catedra Quim. Org.,
Fac. Agron., Univ. Buenos Aires, 4453 Buenos Aires, Argent.; Eng.) —
H. Hoennerscheid
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