Total Synthesis of Epicoccolides A and B by Oxidative Skeleton Rearrangement Leads to a Structural Revision and Questions the Proposed Biosynthesis

The total synthesis of epicoccolides A and B was accomplished by a modular and concise strategy involving a PtCl2-catalyzed alkyne ring cyclization of a highly substituted bis-arylacetylene giving epicoccolide B and an oxidative skeleton rearrangement of this metabolite toward epicoccolide A. Detail...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 27; no. 24; pp. 6539 - 6544
Main Authors Treiber, Tim, Li, Wing-Si, Bingel, Mara, Müller, Anna, Eckhardt, Matthias, Menche, Dirk
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 20.06.2025
Subjects
Alkynes - chemistry
Catalysis
Cyclization
Molecular Structure
Oxidation-Reduction
Polyketides - chemical synthesis
Polyketides - chemistry
Online AccessGet full text
ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/acs.orglett.5c02032

Cover

More Information
Summary:The total synthesis of epicoccolides A and B was accomplished by a modular and concise strategy involving a PtCl2-catalyzed alkyne ring cyclization of a highly substituted bis-arylacetylene giving epicoccolide B and an oxidative skeleton rearrangement of this metabolite toward epicoccolide A. Detailed NMR spectroscopic analysis and data comparisons led to a reassignment of epicoccolide A toward epicocconigrone A, questioning the proposed biosynthesis of these as well as structurally related polysubstituted aromatic polyketides.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.5c02032