Total synthesis of the coccinellid alkaloid (−)-adalinine and the assignment of its absolute configuration

✍ Scribed by Naoki Yamazaki; Toshimasa Ito; Chihiro Kibayashi

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 238 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)02444-7

✦ Synopsis

The first asymmetric total synthesis of a new coccinellid alkaloid (-)-adalinine has been achieved, based on the construction of a 2-piperidone framework with an asymmetric quaternary center at the C-6 position, which was performed by Lewis acid-induced allylation of the cyclic N-acyl-N,O-acetal incorporating the chiral aminophenol auxiliary. This synthesis allowed the absolute stereostructure of natural (-)-adalinine to be assigned as R.