1354536-39-2Relevant articles and documents
Towards the enantioselective synthesis of (-)-euonyminol-preparation of a fully functionalised lower-rim model
Webber, Matthew J.,Warren, Sarah A.,Grainger, Damian M.,Weston, Matthew,Clark, Stacy,Woodhead, Steven J.,Powell, Lyn,Stokes, Stephen,Alanine, Alexander,Stonehouse, Jeffrey P.,Frampton, Christopher S.,White, Andrew J. P.,Spivey, Alan C.
, p. 2514 - 2533 (2013)
The development of a stereoselective total synthesis of β-dihydroagarofuran 4 is described. This compound contains the same oxygenation pattern on its 'lower-rim' as found in the natural sesquiterpene (-)-euonyminol (1) and it is expected that the route described should be applicable to the synthesis of that complex natural product. (-)-Euonyminol is found as the core scaffold of a series of complex macrodilactone sesquiterpenoids isolated from the Celastraceae which possess interesting biological activities (e.g. anti-HIV activity). The synthetic route builds upon an epoxidative asymmetric desymmetrisation of meso-diallylic alcohol 10 that we have reported previously. It features a lactate Ireland-Claisen rearrangement to establish the quaternary stereocentre at C11 (27 → 28a) and an unusual dealkylative intramolecular epoxide-opening by the C11 methyl ether to establish the tetrahydrofuranyl C-ring of the β-dihydroagarofuran skeleton (35 → 36). The Royal Society of Chemistry 2013.