Bio‐inspired Total Synthesis of Twelve Securinega Alkaloids: Structural Reassignments of (+)‐Virosine B and (−)‐Episecurinol A. Issue 49 (13th August 2019)

• Record Type: Journal Article
• Authors: Antien, Kevin; Lacambra, Aitor; Cossío, Fernando P.; Massip, Stéphane; Deffieux, Denis; Pouységu, Laurent; Peixoto, Philippe A.; Quideau, Stéphane
• Is Part Of: Chemistry. Volume 25:Issue 49(2019)
• Page Start: 11574
• Page End: 11580
• Publication Date: 2019-08-13
• Subjects: aldol reaction -- alkaloids -- biomimetic synthesis -- natural products -- total synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201903122
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Abstract : A bio‐inspired sequence of chemical transformations encompassing stereodivergent aldolisation and reductive amination reactions enabled the collective total synthesis of 12 major (neo)(nor)securinanes from the tyrosine metabolite 4‐hydroxyphenylacetic acid. More than 10 years after their isolation, the structure of two neosecurinanes, virosine B and episecurinol A, are herein reassigned.