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The Plakotenins: Biomimetic Diels–Alder Reactions, Total Synthesis, Structural Investigations, and Chemical Biology
Author(s) -
Bourcet Emmanuel,
Kaufmann Larissa,
Arzt Stephanie,
Bihlmeier Angela,
Klopper Wim,
Schepers Ute,
Bräse Stefan
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201201585
Subject(s) - natural product , diastereomer , total synthesis , diels–alder reaction , biomimetic synthesis , chemistry , chemical synthesis , chemical biology , stereochemistry , organic chemistry , biochemistry , catalysis , in vitro
The total synthesis of plakotenin, a cytotoxic marine natural product, using a biomimetic Diels–Alder reaction is described in detail. Two approaches were used, whereby the Diels–Alder reaction occurs at different stages of the synthesis. Homo ‐ and nor ‐plakotenin, related natural products, were also prepared, as well as iso ‐plakotenin, a diastereoisomer of plakotenin. The syntheses prove the relative and absolute stereochemistry of the latter. The chemical biology of the plakotenins was investigated on selected compounds.