Controlled syntheses of 12-oxo-PDA and its 13-epimer

✍ Scribed by Yuichi Kobayashi; Michitaka Matsuumi

• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 77 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)00786-4

✦ Synopsis

Stereoselective synthesis of 12-oxo-PDA starting with (1R,3S)-cyclopenten-1,3-diol monoacetate is accomplished. Key transformations are copper-catalyzed installation of the C(1)-C(8) chain onto the cyclopentene ring and construction of the C(14)-C(18) chain. Similarly, 13-epi-12-oxo-PDA was synthesized, and its [h] D was used to confirm the purity of 12-oxo-PDA (>95%) obtained by 1 H NMR spectroscopy. In addition, stability of 12-oxo-PDA was investigated to eliminate possibility of epimerization to the 13-epimer.