120591-23-3Relevant articles and documents
Application of [3+2] nitrile oxide cycloaddition chemistry to the construction of retinoid skeleton and to a new formal synthesis of (±)-ascofuranone and geiparvarin
Baraldi,Bigoni,Guarneri,Manfredini,Pollini,Simoni
, p. 1515 - 1529 (2007/10/02)
A flexible approach to the construction of the C-20 retinoid carbon skeleton involving the intermolecular [3+2] cycloaddition of the nitrile oxide derived from a C-14 aldehyde component with both a C-6 diene or enyne dipolarophiles, followed by Mo(CO)6-promoted ring opening of the derived 3,5-disubstituted-isoxazoline or -isoxazole ring systems, has been accomplished. The same strategy has been also successfully applied as a tool for the crucial carbon-carbon bond forming step to the formal synthesis of (±)-ascofuranone and to a new synthesis of geiparvarin.