Journal of Organic Chemistry p. 2451 - 2457 (1990)
Update date:2022-08-04
Topics:
Gasparini, Fabrizio
Vogel, Pierre
(1R,2S,4R)-2-Cyano-7-oxabicyclo<2.2.1>hept-5-en-2-yl (1S')-camphanate (5) has been converted into 2,5-anhydro-3-deoxy-D-ribo-hexonic acid (8, eight steps, 38percent) and 2,5-anhydro-3-deoxy-D-xylo-hexonic acid (9, seven steps, 40percent).Similarly, (1S,4S)-7-oxabicyclo<2.2.1>hept-5-en-3-one ((-)-6, derived from (1S,2R,4S)-2-cyano-7-oxabicyclo<2.2.1>hept-5-en-2-yl (1R')-camphanate (7) was converted into 2,5-anhydro-4-deoxy-D-ribo-hexonic acid (10, nine steps, 29percent) and 2,5-anhydro-4-deoxy-D-xylo-hexonic acid (11, eight steps, 31percent).The methods exploit the high regioselectivity of the electrophilic additions of the C=C double bonds in 7-oxabicyclo<2.2.1>hept-5-en-2-yl derivatives 5 and 7 ("naked sugars") and the high exo-face preference for the hydride reduction of 5- and 6-chloro-7-oxabicyclo<2.2.1>hept-5-en-2-ones (21,35). 2'-Deoxyadenosine-C (12) and cordycepin-C (14) were derived from 8 and 10, respectively.Similarly, the corresponding 2'- and 3'-epimers 13 and 15 (C-nucleosides deriving from 2-deoxy- and 3-deoxy-β-D-threo-pentofuranose, respectively) were obtained in few steps and with high stereoselectivity from 9 and 11, respectively.
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Doi:10.1016/S0040-4039(00)97105-3
(1990)Doi:10.1002/ejoc.201501300
(2016)Doi:10.3390/molecules16076129
(2011)Doi:10.3109/14756366.2012.663364
(2014)Doi:10.1021/ol201618f
(2011)Doi:10.1016/S0040-4020(01)90067-5
(1990)