501909-24-6Relevant academic research and scientific papers
Exploiting multiple nucleophilic sites on pyrrole for the assembly of polyheterocyclic frameworks: Application to a formal total synthesis of (±)-aspidospermidine
Banwell, Martin G.,Smith, Jason A.
, p. 2613 - 2618 (2002)
The tricyclic ketone 19, an advanced intermediate in Aube's recently reported synthesis of aspidospermidine (4), is prepared in twelve steps from pyrrole (3). The key transformations involve a previously described intramolecular Michael addition reaction of pyrrole 10 and intramolecular Friedel-Crafts type cyclisation of the derived carboxylic acid 15 to ketone 16. Careful hydrogenation of this last compound afforded the fully saturated alcohol 17 which was readily oxidised to the target ketone 19.
Total synthesis of (±)-rhazinal, an alkaloidal spindle toxin from Kopsia teoi
Banwell, Martin G.,Edwards, Alison J.,Jolliffe, Katrina A.,Smith, Jason A.,Hamel, Ernest,Verdier-Pinard, Pascal
, p. 296 - 305 (2007/10/03)
The title alkaloid I and its B-nor-congener 3, both of which display potent and unusual anti-mitotic properties, have been synthesized in racemic form and characterised by single-crystal X-ray analysis.
