Synthesis of (±)??Nephromopsinic,(−)??Phaseolinic, and (−)??Dihydropertusaric Acids

A Brecht??Forster, J Fitremann…

Index: Brecht-Forster, Andrea; Fitremann, Juliette; Renaud, Philippe Helvetica Chimica Acta, 2002 , vol. 85, # 11 p. 3965 - 3974

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Citation Number: 36

Abstract

Abstract 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 ...