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Chemical Insights into the Anchinopeptolide Series
Author(s) -
Bastos Lemos Silva Siguara,
Beniddir Mehdi A.,
Gallard JeanFrançois,
Poupon Erwan,
Thomas Olivier P.,
Evanno Laurent
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900625
Subject(s) - chemistry , cyclobutane , sponge , intramolecular force , epimer , cycloaddition , stereochemistry , derivative (finance) , congener , ring (chemistry) , organic chemistry , catalysis , botany , biology , financial economics , economics
The chemical composition of the marine sponge Phorbas tenacior was investigated in depth. The anchinopeptolides A–D bearing a central pyrrolidinone were isolated together with a new congener named anchinopeptolide E corresponding to an epimer of anchinopeptolide C. The relative configuration of the central core of anchinopeptolide E was determined by extensive NMR analyses. Additionally, the previously isolated cyclobutane derivative cycloanchinopeptolide C was not detected from the sponge extract but could be synthesised by a photoinduced intramolecular [2+2] cycloaddition giving convincing evidence for its artefactual origin.