Total synthesis of PI-201, a new platelet aggregation inhibitor : Establishment of its absolute stereochemistry

✍ Scribed by Kin-ichi Tadano; Takeshi Murata; Toshihito Kumagai; Seiichiro Ogawa

• Book ID: 104215915
• Publisher: Elsevier Science
• Year: 1993
• Tongue: French
• Weight: 273 KB
• Volume: 34
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)79308-7

✦ Synopsis

Inuamolecular DiebAlder cyckmddition of enantiomerically enriched triene 16 could be attained under thermal conditions resulting in the formation of octahydronaphthalene derivatives 17-20, one of which was convexted into PI-201 (1) , a new platelet aggregation inHibitor. Quite recently, Hanada et al. isolated and characterized PI-201 (1) and PI-200 (2) (Fig. 1) from the fermentation broth of Streptomyces sp. Al498. 1 These compounds were found to be new ADP-induced aggregation inhibitors of rabbit platelets with an ICSO of 7.1 x 104 M and 3.8 x 104 M, respectively. The structures of 1 and 2 were elucidated by spectral means (IH, IT, IR, W, and MS), and finally the relative stenochemistry of 1 was confirmed by a single-crystal X-my analysis. The structure of 2, lactone farm of the shydroxy carboxylic acid 1, was determined by the spectral cormlation to 1.2 Herein, we wish to disclose the first enantioselective total synthesis of 1. The present synthesis verified the unsettled absolute stereochemistry of 1 as shown in Fig. 1.