Solanum alkaloids, 117. Synthesis of the steroid alkaloid soladunalinidine and other 5α-spirosolan-3-amines

✍ Scribed by Quyen, Le Thi ;Ripperger, Helmut ;Schreiber, Klaus

• Publisher: John Wiley and Sons
• Year: 1990
• Tongue: English
• Weight: 674 KB
• Volume: 1990
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199019900199

✦ Synopsis

Abstract

The steroid alkaloid soladunalinidine [5α‐tomatidan‐3β‐amine, (25__S__)‐5α,22β__N__‐spirosolan‐3β‐amine, 2], isolated from Solanum dunalianum, is synthesized from tomatidine (5α‐tomatidan‐3β‐ol, 1) via 5α‐tomatidan‐3‐one (4) and its oxime 5 which is reduced to 2 as well as to its ring‐E‐opened (22__S__) and (22__R__) dihydro products 6 and 9, the N(22,26)‐chloro‐N(3)‐(2‐hydroxy‐benzylidene) derivatives 8 and 11 of which are recyclized to N(3)‐(2‐hydroxybenzylidene)soladunalinidine (3). The 5α‐spirosolan‐3‐amines stereoisomeric at C‐22 and C‐25, 5α‐solasodan‐3α‐amine (13) and ‐3β‐amine (15), are obtained in an analogous sequence of reactions from soladulcidine (5α‐solasodan‐3β‐ol, 12).