Total synthesis of thromboxane B2 starting from (R,R)-tartaric acid as a chiral pool

Article abstract of DOI:10.1016/S0040-4039(97)82953-X

Optically active natural thromboxane B₂ (TXB₂) was synthesized from (R,R)-tartaric acid as only chiral source. The synthesis was achieved through regio- and stereoselective introduction of acetate moiety at the C2-position of the 6,8-dioxabicyclo[3.2.1]octene derivative (2) to provide an acetamide derivative (6), partial ring opening of 6 to give a pyranoid (10), and construction of the C15-hydroxyl group of TXB₂ by stereospecific allylic transposition of the inherent chirality of tartaric acid in the transallylic acetate (18).