221354-52-5Relevant articles and documents
The synthesis of a natural product family: From debromoisolaurinterol to the aplysins
Harrowven, David C,Lucas, Matthew C,Howes, Peter D
, p. 791 - 804 (2007/10/03)
Total syntheses of (±)-aplysin 1, (±)-debromoaplysin 2, (±)-isoaplysin 3, (±)-aplysinol 4, (±)-debromoaplysinol 5, (±)-aplysinal 6, (±)-isolaurinterol 7 and (±)-debromoisolaurinterol 8 are described. Key features are a diastereoselective, sulfur mediated radical cyclisation of diene 12 to give 35; a new radical to polar crossover sequence mediated by Bu3Sn that transforms diene 12 into (±)-debromoisolaurinterol 8; and a series of biomimetic cyclisation and oxidation reactions.
Total syntheses of aplysin and debromoaplysin using a diastereoselective, sulfur mediated radical cyclisation strategy
Harrowven, David C.,Lucas, Matthew C.,Howes, Peter D.
, p. 4443 - 4444 (2007/10/03)
Total syntheses of two marine sesquiterpenes, aplysin 1 and debromoaplysin 2, are described. The key step involves a diastereoselective, sulfur mediated radical cyclisation of diene 5 to 7 which simultaneously creates the sterically demanding aplysin skeleton and establishes the relative configuration of the three contiguous stereogenic centres.
