A novel synthesis of cis-3,4-disubstituted cyclopentanones

✍ Scribed by K. Sakai; Y. Ishiguro; K. Funakoshi; K. Ueno; H. Suemune

• Book ID: 104232521
• Publisher: Elsevier Science
• Year: 1984
• Tongue: French
• Weight: 197 KB
• Volume: 25
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)80074-5

✦ Synopsis

A new method for the stereospecific synthesis of cis-3,4-disubstituted cyclopentanones is described. 4s a part of synthetic studies on biologically active compounds consisting of five membered ring such as prostaglandins, brefeldin A and methylenomycin A, we undertook the stereospecific synthesis of cis-3,4-disubstituted cyclopentanones. Previously,we reported on the new cyclization reactionl)( Scheme 1 ) catalyzed by tris(triphenylphosphine)rhodium[I] chloride (Wilkinson complex), in which 2,3_disuhstituted 4-pentenals could be cyclized to 2,3-disubstituted cyclopentanones accompanied by the formation of cyclopropane derivatives under mild conditions. However,the formations of cyclopentanones resulted in unsatisfactory yield. Later, the similar reactions using Rh-complex were independently studied by R.G.Miller 2) 3) and R.C.Larock

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