A photochemical approach to the 11-deoxyprostaglandin intermediate

✍ Scribed by Toshio Ogino; Kazuyoshi Yamada; Koji Isogai

• Publisher: Elsevier Science
• Year: 1977
• Tongue: French
• Weight: 219 KB
• Volume: 18
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)83789-8

✦ Synopsis

Several recent papers have reported effective syntheses of 11-deoxyprostaglandins using the la&one aldehyde _l_ as a key intermediate 1) 2) .' In connection with our previous report 3) on the photoannelation reaction of 5-methyl-2,3-dihydro-3-furanone with olefins, we wish to describe in this letter a simple three-step synthesis of the lactone 1 and its 11-oxa-12-methyl analogue P) starting from photochemical cycloaddition of methyl 6-acetoxyacrylate to 2-cyclopentenone and 5-methyl-2,3-dihydro-3-furanone. In spite of the synthetic or mechanistic interest in the regioselectivity of the photochemical cycloaddition reaction of B-alkoxy-or Bacyloxyacrylic acid esters with cyclic enone, there have been no reports as to the photochemical reaction of this type of olefin with cyclic enone.