Premium
Synthesis of (±)‐Nephromopsinic, (−)‐Phaseolinic, and (−)‐Dihydropertusaric Acids
Author(s) -
BrechtForster Andrea,
Fitremann Juliette,
Renaud Philippe
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200211)85:11<3965::aid-hlca3965>3.0.co;2-2
Subject(s) - chemistry , bicyclic molecule , cleavage (geology) , iodide , stereochemistry , organic chemistry , combinatorial chemistry , geotechnical engineering , fracture (geology) , engineering
The formal syntheses of (±)‐nephromopsinic acid, (−)‐phaseolinic acid, and the first total synthesis of (−)‐dihydropertusaric acid from (±)‐ and (−)‐7‐oxabicyclo[2.2.1]hept‐5‐en‐2‐one are described. These syntheses take advantage of a previously reported radical rearrangement (1,2‐acyl migration). A remarkable iodide‐mediated cleavage of a bicyclic system, followed by the introduction of the γ ‐chains via a mixed Kolbe electrolysis, are the key steps of these syntheses. This approach is general and could be applied for the preparation of all kinds of paraconic acids with excellent control of the stereochemistry.