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The first example of a highly stereoselective intramolecular radical cyclisation of a cyclopentenol derivative

✍ Scribed by Paul R. Jenkins; Andrew J. Wood

Book ID: 104256583
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 186 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)00211-6

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✦ Synopsis

Silyl methylene radical cyclisation of a ~allylic cyclopentannnulated derivative of glucose leads to a single cis fused tricyclie ring system whereas the same cyclisation of the corresponding derivative leads to a mixture of cis and trans fused products. These results can be explained by the preference for the formation of the cis fused 5,6-ring system even when this does not involve reaction from the least hindered side of the molecule.

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