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A general stereocontrolled route to carbocyclic C-nucleosides: (±) carba-showdowmycin

✍ Scribed by Anil K. Saksena; Ashit K. Ganguly

Book ID
104243583
Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
229 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis

Novel dithiotosylate-mediated C-C ring scission reactions l-t2 and 24+5 conve--niently made available synthons towards a host of carbocyclic analogs-o? C-nucleosides. Unlike the past work,4 no chemoselectivity problems arose in generation of 15. -The broad spectrum C-nucleoside antibiotics produced by several Streptomyces species continue to be of great synthetic interest.' Suitably protected cl-ketoesters have been featured as key intermediates in the first elegant syntheses of showdowmycin,'a-c pyrazomycin3 and their important relatives.

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A general, stereocontrolled entry to pyr
A general, stereocontrolled entry to pyrimidine homo-C-nucleosides
✍ T. Sato; K. Marunouchi; R. Noyori 📂 Article 📅 1979 🏛 Elsevier Science 🌐 French ⚖ 234 KB

A simple synthesis of nucleoside analogues with a methylene group between the ribose and B-position of pyrimidine appendages is outlined. The unique activities displayed by the homonucleotides I and II2 prompted us to prepare homo -C-nucleosides,