Iridoids from Carbohydrates via Pauson-Khand Reaction: Synthesis of Advanced Highly Oxygenated Cyclopentane-Annulated Pyranosides from D-Glucal Derivatives.
The Pauson-Khand reaction on suitable 4-oxa-hept-1-en-6-ynes (1, 17) obtained from 3,4,6-tri-O-acetyl-D-glucal gives the cyclopentane-annulated pyranosides (2, 18) that can be efficiently and stereoselectivelly transformed into chiral, advanced, highly oxygenated intermediates (10, 16, 24) for the synthesis of iridoid aglycones.
Marco-Contelles
José
J
Instituto de Química Orgánica General (CSIC), Laboratorio de Radicales Libres, C/Juan de la Cierva, 3; 28006-Madrid, Spain.
Ruiz-Caro
Juliana
J