title: Towards the enantioselective synthesis of (-)-euonyminol--preparation of a fully functionalised lower-rim model.
abstract: 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).
authors: Department of Chemistry, South Kensington Campus, Imperial College, London SW7 2AZ, UK.
authors: Matthew J
authors: MJ
authors: Webber
authors: Sarah A
authors: SA
authors: Warren
authors: Damian M
authors: DM
authors: Grainger
authors: Matthew
authors: M
authors: Weston
authors: Stacy
authors: S
authors: Clark
authors: Steven J
authors: SJ
authors: Woodhead
authors: Lyn
authors: L
authors: Powell
authors: Stephen
authors: S
authors: Stokes
authors: Alexander
authors: A
authors: Alanine
authors: Jeffrey P
authors: JP
authors: Stonehouse
authors: Christopher S
authors: CS
authors: Frampton
authors: Andrew J P
authors: AJ
authors: White
authors: Alan C
authors: AC
authors: Spivey
mesh_terms: D060326:Chemistry Techniques, Synthetic; D005663:Furans / Q000737:chemistry; D008956:Models, Chemical; D010100:Oxygen / Q000737:chemistry; D020005:Propanols / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D005663:Furans; D020005:Propanols; D012717:Sesquiterpenes; C006463:allyl alcohol; D010100:Oxygen; C039281:furan