25472-13-3Relevant academic research and scientific papers
Bio-inspired Total Synthesis of Twelve Securinega Alkaloids: Structural Reassignments of (+)-Virosine B and (?)-Episecurinol A
Antien, Kevin,Cossío, Fernando P.,Deffieux, Denis,Lacambra, Aitor,Massip, Stéphane,Peixoto, Philippe A.,Pouységu, Laurent,Quideau, Stéphane
supporting information, (2019/08/21)
The so-called Securinega alkaloids constitute a class of tetracyclic biologically active specialised metabolites isolated principally from subtropical plants belonging to the Phyllanthaceae family. Following a strategy based on alternative hypotheses for their biosynthesis, an easy and time-efficient divergent synthesis enabled access to twelve of those alkaloids featuring (neo)(nor)securinane skeletons. Moreover, this work permitted to reassign the absolute configurations of (+)-virosine B and (?)-episecurinol A.
Synthesis of the Securinega Alkaloids (+/-)-Norsecurinine and (+/-)-Nirurine from 3-Hydroxypyridine
Magnus, Philip,Rodriguez-Lopez, Julian,Mulholland, Keith,Matthews, Ian
, p. 8059 - 8072 (2007/10/02)
Treatment of the dihydropyridine 5 with fluoride anion resulted in in situ formation of the allenylidene 4 which cyclized to the azabicyclooctene 9.Subsequent elaboration to the alcohol 24 and rearrangement gave norsecurinine 2.The intermediate dio
TOTAL SYNTHESIS OF (+/-)-NORSECURININE
Heathcock, Clayton H.,Geldern, Thomas W. von
, p. 75 - 78 (2007/10/02)
The structures of the enantiomeric norsecurinines (2 and 3) have been confirmed by a total synthesis of (+/-)-2, starting with L-proline.
