Synthesis of punaglandin 4 by means of enzymatic resolution of the key chlorocyclopentene derivative

✍ Scribed by Kenji Mori; Tadashi Takeuchi

• Book ID: 104203530
• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 814 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)85825-7

✦ Synopsis

Abet?ZaCt --RmagkttXh 4, a chlorUtated tnarxne prosteno~d, we ~ynthi?~lPed EtWklng from two cbxal b.azldmg blocks. t+l-tartarrc acxd and (1~4R_)-[-)-ri-t_butyldlmethylss:yloxy-3-chloro-2-~l~te+l-o1, whxh we8 prepared by asymmetrx hydrolyss of the mnespmdmg (*)-acetate rnth pg pancreatic lqmee. Punaglandin 4 (PUG 4, la) is one of the chlorinated marine prostanoids isolated from the Hawaiian octocoral Telesto riisei by Scheuer and his co-workers.' Its remarkable antitumor activity together with its unique structure attracted attention of chemists, and two independent syntheses by Yamada et al ' and by Noyori et al 3 appeared soon after --* ---Scheuer's structural proposal. Their works established the correct stereostructure of PUG 4 as depicted in la. Another synthesis was reported recently by Sasai and Shibasaki.l We