Stereoselective Synthesis of Substituted Piperidines – Total Synthesis and Absolute Configurations of (+)- and (–)-Dienomycin C

✍ Scribed by Isabelle Ripoche; Jean-Louis Canet; Jacques Gelas; Yves Troin

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 297 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199907)1999:7<1517::aid-ejoc1517>3.0.co;2-h

✦ Synopsis

The first total asymmetric synthesis and the attribution of the tricarbonyl(dienal)iron complex (+)-4 which is easily obtained by separating preformed diastereomers, starting absolute configurations of (+)-dienomycin C (1), an alkaloid isolated from a Streptomyces strain, are reported. This from phenylpentadienoic acid and (S)-methyl mandelate. compound was prepared in six steps from the enantiopure antibiotic activity against Mycobacteria. [6b] This alkaloid is allowed a facile (∆R f ϭ 0.08 vs. 0.04) large-scale prep-