Totalsynthese von (+)-3-Oxacarbacyclin mittels asymmetrischer Olefinierungs- und Deprotonierungs-Reaktionen

摘要

(+)-3-Oxacarbacyclin was synthesized by a stereoselective 18 steps total synthesis with a total yield of 1.5%. The most important steps were the asymmetric Horner-Wadsworth-Emmons olefination and the asymmetric deprotonation. Five chiral phosphonates and amides were synthesised and the enantioselektivities and diastereoselektivities under different reaction conditions were figured out. The optimized conditions were utilized in the total synthesis and the (+)-3-Oxabarcacyclin could be gained diasteromeric pure with ee > 99.4%.