Asymmetric synthesis of cyclohexene nucleoside analogues.

The Journal of organic chemistry (2011-08-26)
Sylvain Dalençon, Ramzi Aït Youcef, Muriel Pipelier, Vincent Maisonneuve, Didier Dubreuil, François Huet, Stéphanie Legoupy
ABSTRACT

The asymmetric synthesis of novel cyclohexene nucleoside analogues 12 and 15 is described. An enantiospecific Diels-Alder reaction between (E,E)-diene 2 and (+)-5-(d-mentyloxy)-2(5H)-furanone 3 provided the cycloadduct isomer 4. Three additional steps yielded amine 8 allowing the constructions of the thymine and adenine moieties to afford intermediates 11 and 14, respectively. Amination or cyclization and removal of the protecting groups occurred in one step in the presence of ammonia, giving the target six-membered ring nucleosides.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Cyclohexene, contains 100 ppm BHT as inhibitor, ≥99.0%
Sigma-Aldrich
Cyclohexene, inhibitor-free, ReagentPlus®, 99%
Supelco
Cyclohexene, analytical standard

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