No abstract

No abstract

No abstract

The feasibility of using the Mitsunobu reaction for coupling of purines with steroids to obtain nucleosteroids was investigated in the particular case of 6‐chloropurine and cholesterol. Three principal products were obtained: 3βbT‐(6‐chloropurin‐9‐yl)‐5‐cholestene (1), 3α‐(6‐chloropurin‐9‐yl)‐5‐cholestene (2), and 6βbT‐(6‐chloropurin‐9‐yl)‐3,5‐cyclocholestane (3), isolated with 10.5%, 22.7%, and 12.6% yield, respectively. The stereochemical and structural diversity of the coupling products are explained by the formation of a homoallylic carbocation through participation of the double bond of cholesterol.