Access to Thromboxane Compounds: Syntheses from Carbohydrates, as Natural Chiral Pools

The cascade of biosynthetic products1,2 derived from arachidonic acid involves several oxygenated heterocycles, including thromboxanes A2 and B2 (in the following TXA2 and TXB2, respectively, Scheme 1). In the biological pathway TXA2 (1) is produced directly from prostaglandin H2 (PGH2, 2), and this same compound is the common precursor of the previously known prostaglandins (i.e. PGE2, PGF2a and PGD2, etc.), as well as of the more recently discovered “beneficial” prostaglandin I2 (PGI2, 3). Upon hydrolysis under biological conditions TXA2 (1) is converted into the more stable thromboxane B2 (TXB2,4).