A new synthesis of spirobenzylisoquinolines. Analogues of sibiricine and corydaine

✍ Scribed by Herbert L. Holland; David B. MacLean; Russell G.A. Rodrigo; Richard F.H. Manske

• Book ID: 104224250
• Publisher: Elsevier Science
• Year: 1975
• Tongue: French
• Weight: 152 KB
• Volume: 16
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)91114-6

✦ Synopsis

The reduction product of dehydrocordrastine, 2, with di-isobutylaluminum hydride spontaneously rearranged to the spirobenzylisoquinolines 7a and 7b, analogous to the alkaloids hr ry sibiricine (5a), corydaine (21, and yenhusomidine (2).

N

Previous syntheses (1) of spirobenzylisoquinline alkaloids (2) have led to compounds with symmetrical substitution in ring C, such as ochrobirine (&I, compounds with only a single carbon substituent in that ring, such as ochotensine (Za) and ochotensimine ( ). or to monow oxygenated compounds such as fumaricine (3a), fumaritine (3b), and fumariline (4) (2). CI w