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Fragmentation of alkoxy radicals: Mechanistic aspects of the tandemβ-fragmentation-intramolecular functionalization reaction

✍ Scribed by R Hernández; J.J Marrero; E Suárez; A Perales

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 278 KB
Volume: 29
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)82245-5

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✦ Synopsis

The formation of the B-peroxylactone (4) &ring the photolysis of lactol (3)

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with (diace@yiodo)-benzene (DIB) and iodine under oxygen atmosphere a!emostrates the presence of a peroxyradical intermediate in the tandem p-fragmentation-intramolecularfunctionalization reaction.

We have recently reported that photolysis of intramolecular hemiketals in the presence of a hypervalent iodine reagent and iodine leads to alkoxy radicals which undergo p-fragmentation to produce lactones in good yield.la This approach has been applied to the syntheses of models of A and A rings of limonin lb and ring A of vemolepin.

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