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Stereoselective C-C bond formation in carbohydrates by radical cyclization reactions-II

✍ Scribed by Alain De Mesmaeker; Pascale Hoffmann; Beat Ernst

Book ID
104232765
Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
214 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

The synthesis of the bicyclic acetals 8 from the glycal 1 us reaction is described_ Intensive work has been devoted to the synthesis of C-branched sugars ng a radical cyclization -3) _ We have recently reported '1 an efficient and stereoselective synthesis of the a-C(Z) branched pyranosides 5 by radical cyclization reaction (2 -4: scheme). The radical acceptor (C=C) is part of the -pyranosidic ring and the initial radical 3 is generated on the glycosidic side chain. The -crucia1 final ring scission of the bicyclic acetal 4 is performed with acetyl chloride in the presence of a catalytic amount of CoC12. AcO 33 Ac0110.

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