Parallel modification of tropane alkaloids

✍ Scribed by Nicholas S Aberle; A Ganesan; John N Lambert; Simon Saubern; Reg Smith

• Book ID: 104230114
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 84 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)00028-4

✦ Synopsis

Various tropane alkaloids have been prepared by structural modification of the readily available natural product, scopolamine 1. Reaction of isocyanates with 6,7-dehydrotropine 5 provided a number of urethanes 6a-e. Reductive amination of tropinone 7 and subsequent reaction with isocyanates provided ureas 9a-f. Mitsunobu inversion of the C-3 alcohol of tropine 10 afforded the epimeric ester 11.