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C-nucleosides and related compounds X synthesis of the carbocyclic analogues of D, L-pyrazofurin a (pyrazomycin) and showdomycin

✍ Scribed by George Just; Sunggak Kim

Publisher: Elsevier Science
Year: 1976
Tongue: French
Weight: 156 KB
Volume: 17
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)93751-1

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✦ Synopsis

Pyrazofurin A (VIII) and showdomycin (IV) are nucleosides havin? marked antiviral, antibacterial and antitumor activity2, and their syntheses have been re-ported3r4.

We should like to describe the synthesis of their carbocyclic analogues IX and V.

The readily available olefin ester I 5 was ozonolyzed in methylene chloride at -78O. Dimethylsulfide reduction 6, followed by reduction with two-fold excess of tri-t-butoxyaluminum hydride in tetrahydrofuran save diol ester II5 in 60 -65% yield, based on I. Pivaloylation with 1.1 eq of pivaloyl chloride in pyridine/ methylene chloride gave the monopivalate IIb in 80% yield as an oil.

Similarly, the t-butyldimethyl silyl ether IIa could be formed in 80% yield by the addition of 1.1 eq of t-butyl-dimethyl silyl chloride, 2.5 eq of imidazole in dimethylformamide at 20' for 24 hrs.7

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