Auxiliary-controlled stereoselective enolate protonation: Enantioselective synthesis of cis and trans annulated decahydroquinoline alkaloids

✍ Scribed by Markus Weymann; Martin Schultz-Kukula; Horst Kunz

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 194 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)01745-6

✦ Synopsis

The diastereoselective synthesis of the octahydroquinoline enone precursor of pumiliotoxin C is achieved via tandem Mannich-Michael reaction on N-galactosyl imines. Conjugate euprate addition to the bicyclic enone stereoselectively forms the trans annulated 4a-epi-purmliotoxin C skeleton in the presence of the carbohydrate auxiliary, and the cis annulated pumiliotoxin C skeleton in its absence.