|
|||||
|
|
Bio-inspired Total Synthesis of Twelve Securinega Alkaloids: Structural Reassignments of (+)-Virosine?B and (?)-Episecurinol?A |
|
| Authors: | Dr Kevin Antien Dr Aitor Lacambra Prof Fernando P Cossío Dr Stéphane Massip Dr Denis Deffieux Prof Laurent Pouységu Dr Philippe A Peixoto Prof Stéphane Quideau |
| Institution: | 1. Univ. Bordeaux, ISM (CNRS-UMR 5255), 351 cours de la Libération, 33405 Talence Cedex, France;2. Univ. Bordeaux, ISM (CNRS-UMR 5255), 351 cours de la Libération, 33405 Talence Cedex, France
Departamento de Química Orgánica I, Universidad del País Vasco, Avda. Tolosa 72, Edificio Korta, 20018 San Sebastián, Spain;3. Departamento de Química Orgánica I, Universidad del País Vasco, Avda. Tolosa 72, Edificio Korta, 20018 San Sebastián, Spain;4. Univ. Bordeaux, Institut Européen de Chimie et Biologie (CNRS-UMS 3033), 2 rue Robert Escarpit, 33607 Pessac Cedex, France |
| Abstract: | 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. |
| Keywords: | aldol reaction alkaloids biomimetic synthesis natural products total synthesis |