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Nucleosteroids: Synthesis of purinyl‐steroid derivatives under mitsunobu reaction conditions
Author(s) -
Cadenas Raúl A.,
Gelpi María E.,
Mosettig Jorge
Publication year - 2005
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570420101
Subject(s) - chemistry , carbocation , yield (engineering) , mitsunobu reaction , steroid , purine metabolism , stereochemistry , double bond , coupling reaction , medicinal chemistry , organic chemistry , biochemistry , enzyme , materials science , metallurgy , catalysis , hormone
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.