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Carbocyclic analogs of C-nucleosides: a key intermediate via a novel and efficient CC ring scission

✍ Scribed by Anil K Saksena; Andrew T McPhail; Kay D Onan

Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
220 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis

Treatment of hydroxymethylene ketone 5 with trimethylene dithiotosylate according to literature conditions, 3b led to the novel C-C ring scission product 7 in high yield; also, _ the hydroxide-initiated cleavage4 of 1 gave the S-elimination product 13 which underwent a highly stereospecific addition of diazomethane to provide 15. -C-Glycosyl nucleosides comprise an important group of naturally-occurring substances represented by the broad spectrum antibiotics showdowmycin, pyrazomycin, formycins, and oxazinomycin (or minimicin). 1 Previously, we reported on a convenient route to carbocyclic analogs of conventional A-glycosyl nucleosides. 2 We here describe our progress towards a general route to carbocyclic C-nucleosides.

Of the several bicyclo[2.2.l]heptane systems which we considered as precursors, the a-diketone monothioketal 1 appeared to be the most appropriate.

In addition to its possible availability from 3 by well-known procedures, 3 we envisioned that the hydroxide-initiated _ cleavage

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