Synthesis and absolute configuration of the naturally occurring cyano glucoside simmondsin
Abstract
The synthesis of the naturally occurring cyano glucoside simmondsin, 1, is reported. An optically active cyclitol, L-quebrachitol 2, was stereoselectively converted into the aglycone 19, which was condensed with D-glucose, followed by deprotection to provide simmondsin 1. This synthesis successfully determined the absolute configuration of the natural product.