Synthesis of thromboxane A2 analog dl-(9,11),(11,12)-dideoxa-(9,11),(11,12)-dimethylene thromboxane A2

✍ Scribed by Shuichi Ohuchida; Nobuyuki Hamanaka; Masaki Hayashi

• Publisher: Elsevier Science
• Year: 1979
• Tongue: French
• Weight: 215 KB
• Volume: 20
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)95491-7

✦ Synopsis

The thromboxane A2 analog, dl-(9,11),( 11,12)-dideoxa-(9,11),(11,12)dimethylene thromboxane A2 (TX A2) has been synthesized; the compound showed high agonist activities on platelet aggregation and the aorta contracting activities. In 1975, Samuelsson et al. discovered a new family of arachidonic acid cascade, thromboxane A2, from incubation products of arachidonic acid and human platelets.' 'Ihissubstancewas extremely labile and highly biologically active. Although the whole structure of TX A2 has not been confirmed directly yet, formulaLhas been believed as reasonable structure for TX A2 by several trapping experiments affording TX B2 and its derivatives.2 Since the instability and biological importance of TX AZ, synthetic chemists have been focusing on obtaining its stable congeners. In this report, we would like to describe the first synthesis of stable TX A2 analog, dl-(9,11),(11,12)-dideoxa-(9,11),(11,12)-dimethylene TX A2 Lin which oxygen atoms in the cyclic moiety of natural 'IX A2 are replaced by carbon atoms.