Studies on an Oxidative 1,4-Addition to s-trans-1,3-Dienes, a Key Reaction in a Strigol Total Synthesis

• Published in: European journal of organic chemistry Vol. 2003; no. 23; pp. 4640 - 4653
• Main Authors: Galkina, Anna, Buff (née Kranz), Angelika, Schulz (née Samson), Emmanuelle, Hennig, Lothar, Findeisen, Matthias, Reinhard, Gerd, Oehme, Ramona, Welzel, Peter
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.12.2003; WILEY‐VCH Verlag; Wiley
• Subjects: Chemistry; Chemistry, Organic; Olefination; Oxidation; Palladium; Physical Sciences; Science & Technology; Stereochemistry; STEREOISOMERS; PALLADIUM-CATALYZED SUBSTITUTION; HORNER-WITTIG REACTION; oxidation; FORMAL TOTAL-SYNTHESIS; REARRANGEMENT; ALLYLIC ALCOHOLS; stereochemistry; palladium; SYSTEMS; GERMINATION STIMULANT; (+)-STRIGOL; PHOSPHINE OXIDES; olefination

Oxidation of 4,6‐heptadienoic acid systems with hydrogen peroxide in the presence of a catalytic amount of diphenyl diselenide leads to 5‐(3‐hydroxypropenyl)dihydrofuran‐2‐one systems with defined relative configuration at the 4 and 7 positions (carboxylic acid numbering). A system having a six‐memb...