484051-76-5Relevant academic research and scientific papers
Synthesis of vinca alkaloids and related compounds. Part 101: A new convergent synthetic pathway to build up the aspidospermane skeleton. Simple synthesis of 3-oxovincadifformine and 3-oxominovincine. Attempts to produce 15β-hydroxyvincadifformine
éles, János,Kalaus, Gy?rgy,Greiner, István,Kajtár-Peredy, Mária,Szabó, Pál,Szabó, Lajos,Szántay, Csaba
, p. 8921 - 8927 (2002)
A molecule with an indole skeleton, containing a latent acrylic ester function - acting as a diene - was produced from Nb-trityl-2-(hydroxy-methyl)-tryptamine and reacted with esters containing an aldehyde or aldehyde-equivalent structural unit, yielding 3-oxo-16,17-dihydro-Δ20-secodin-17-ol type intermediates from which dehydration, followed by [4+2]cycloaddition, furnished 3-oxovincadifformine and 3-oxominovincine. We also wished to apply the method to produce 15β-hydroxyvincadifformine, however, the appearance of a dimeric product with indole skeleton was observed instead of the expected cycloaddition.
