Total synthesis of (+)-thromboxane B2 from D-glucose. A detailed account

Abstract

The total synthesis of thromboxane B2 from D-glucose is described, based on the recognition of hidden carbohydrate-type symmetry in the molecule. Methyl 2-deoxy-α-D-ribo-hexopyranoside was prepared from D-glucose and manipulated in such a way as to introduce C-branching at C-4 in a stereocontrolled manner. This crucial intermediate was then transformed into the target compound by adaptations of established methodology in the field.