A convenient method for the stereoselective synthesis of diasteroisomeric vinyl epoxides (-)-2α and (-)-2β, the carba analogues of D-galactal and D-allal-derived vinyl epoxides 1α and 1β, has been elaborated starting from tri-O-acetyl-D-glucal. The key step of this synthesis is an application of the known Claisen thermal rearrangement of a glucal derivative, the vinyl allyl ether (+)-3, which allows to switch the glycal structure into the corresponding carba analogue scaffold. Epoxides (-)-2α and (-)-2β derive from the same synthetic intermediate, the trans diol (+)-5.
Stereodivergent synthesis of diastereoisomeric carba analogs of glycal-derived vinyl epoxides: A new access to carbasugars
DI BUSSOLO, VALERIA;FAVERO, LUCILLA;PINESCHI, MAURO;CROTTI, PAOLO
2011-01-01
Abstract
A convenient method for the stereoselective synthesis of diasteroisomeric vinyl epoxides (-)-2α and (-)-2β, the carba analogues of D-galactal and D-allal-derived vinyl epoxides 1α and 1β, has been elaborated starting from tri-O-acetyl-D-glucal. The key step of this synthesis is an application of the known Claisen thermal rearrangement of a glucal derivative, the vinyl allyl ether (+)-3, which allows to switch the glycal structure into the corresponding carba analogue scaffold. Epoxides (-)-2α and (-)-2β derive from the same synthetic intermediate, the trans diol (+)-5.File in questo prodotto:
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