Total Syntheses of (+/-)-Cyclophellitol and (1R,6S)-Cyclophellitol.
A stereodivergent synthesis of (+/-)-cyclophellitol (1) and its unnatural diastereoisomer (1R,6S)-cyclophellitol (2), starting from the Diels-Alder adduct of furan and acrylic acid, is reported. The stereochemistry of the key step, the epoxidation of alkene 7, is controlled by the nature of the hydroxyl protecting groups.
Aceña
José Luis
JL
Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense, 28040 Madrid, Spain.
Arjona
Odón
O
Plumet
Joaquín
J