Chemical Insights into the Anchinopeptolide Series. Issue 31 (14th June 2019)

• Record Type: Journal Article
• Authors: Bastos Lemos Silva, Siguara; Beniddir, Mehdi A.; Gallard, Jean‐François; Poupon, Erwan; Thomas, Olivier P.; Evanno, Laurent
• Is Part Of: European journal of organic chemistry. Issue 31/32(2019)
• Page Start: 5515
• Page End: 5518
• Publication Date: 2019-06-14
• Subjects: Anchinopeptolide -- Cycloaddition -- Modified peptides -- Natural products -- Phorbas tenacior; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201900625
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : 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. 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.