6792-12-7Relevant articles and documents
Synthesis of Vinca Alkaloids and Related Compounds. 90.1 New Results in the Synthesis of Alkaloids with the Aspidospermane Skeleton. First Total Synthesis of (±)-3-Oxominovincine
Kalaus, Gy?rgy,Juhász, Imre,Greiner, István,Kajtár-Peredy, Mária,Brlik, János,Szabó, Lajos,Szántay, Csaba
, p. 9188 - 9191 (1997)
The tryptamine derivative 1 readily reacted with methyl 4-acetyl-5-bromopent-4-enoate (9) that had been built up from 2,4-pentanedione. On intramolecular dehydration and subsequent [4 + 2] cycloaddition, the reaction product 10 gave the epimers 12 and 13 having the D-secoaspidospermane skeleton. Compound 12 directly and 13 after epimerization yielded (±)-3-oxominovincine (14). Regioselective reduction of 14 furnished (±)-minovincine (17).
STUDIES IN BIOMIMETIC ALKALOID SYNTHESES-10. THE SYNTHESYS OF A 19-OXOSECODINE AND ITS CYCLIZATION TO MINOVINCINE
Kuehne, Martin E.,Earley, William G.
, p. 3715 - 3718 (2007/10/02)
The synthesis, isolation and characterization of 19-oxo Δ20,21 secodine (2) is described.This compound is first example of a stabilized, potentially reactive secodine intermediate in alkaloid synthesis.It cyclized to minovincine (1) in 77 perce