Prostaglandin chemistry VII A synthesis of new 8-phenylthio-11-deoxyprostaglandins

✍ Scribed by Seizi Kurozumi; Takeshi Toru; Toshio Tanaka; Makiko Kobayashi; Shuji Miura; Sachio Ishimoto

• Publisher: Elsevier Science
• Year: 1976
• Tongue: French
• Weight: 192 KB
• Volume: 17
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)92583-8

✦ Synopsis

SO great

efforts in prostaglandin syntheses have been currently made on the synthesis of novel prostaglandin analogues and on much more convenient synthetic approach to these compounds. Recently, the conjugate addition-enolate trapping method has been used for the short and highly convergent approach to the prostanoids.

l-4 In a previous communication, 5

we have reported synthesis of new 7-oxoprostaglandins using the methodology of the conjugate additionenolate trapping with acyl halides.

In this communication, we wish to describe trapping of organocopper enolate with diphenyl disulfide or benzenesulfenyl chloride, giving new prostaglandin analogues.

Conjugate addition6 of lithium mixed organocuprate 4a 697 to cyclo-pent-Z-en-l-one in ether (-78', 1 hr) gave the R-alkenylated arganocopper enolate which was added to 1.5 eq. of diphenyl disulfide in THF and HMPR (m40-o", 1 hr) to give phenylthio ketone la [38 %; ir (film), 3030, 1740, -