Sulfur-mediated radical cyclisation reactions on solid support
โ Scribed by David C Harrowven; Peter J May; Mark Bradley
- Book ID
- 104252695
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- French
- Weight
- 191 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
Two methods for effecting radical cyclisation reactions of solid-supported 1,6-dienes are described. Additions of thiophenol and p-tolyl benzeneselenosulfonate have each been achieved with a concomitant 5-exo-trig radical cyclisation leading to the formation of highly functionalised cyclopentanes.
๐ SIMILAR VOLUMES
The first examples of intermoleeular free radical allylation reactions on solid support are reported. The allylation proceeds in good chemical efficiency with a variety of substrates as well as allylating agents. Control experiments indicate that the polymer matrix is inert to the reaction condition
Total syntheses of two marine sesquiterpenes, aplysin I and debromoaplysin 2, are described. The key step involves a diastereoselective, sulfur mediated radical cyclisation of diene 5 to 7 which simultaneously creates the stefically demanding aplysin skeleton and establishes the relative configurati