Intramolecular free radical functionalisation of the methyl group of 5′-deoxyadenosine
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 12,p. 3065-3069
- https://doi.org/10.1039/p19810003065
Abstract
Formation (2 methods) of a free radical at the 8-position of 5′-deoxy-2′,3′-O-isopropylideneadenosine causes cyclisation with the 5′-methyl group to give, in yields of up to 80%, 5′-deoxy-2′,3′-O-isopropylidene-5′,8-cycloadenosine, identical with the product formed from the 5′-radical by cyclisation with the 8-position. The reactions provide an in vitro analogy for the functionalisation of the methyl group of 5′-deoxyadenosine postulated as a step in the mechanism of many enzymic coenzyme B12-controlled rearrangement reactions.Keywords
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