Lessons learned from macrolide synthesis.
The highlights of three macrolide syntheses recently completed in our laboratory are described. In the epothilone B synthesis we developed the "early epoxide approach," which resulted in the first completely stereocontrolled synthesis of this natural product. In the laulimalide synthesis our contribution was the auxiliary controlled ene-macrocyclization and Sharpless' kinetic resolution for achieving a regioselective epoxidation of two pseudo-enantiomorphic allylic alcohol subunits. The tartrolon B synthesis was the first to be completed. In this case, a substrate controlled aldol addition was used to assemble the entire carbon skeleton of the compound.
Mulzer
Johann
J
Institut für Organische Chemie der Universität Wien, Währinger Strasse 38, A-1090 Wien, Austria. Johann.Mulzer@univie.ac.at
Martin
Harry J
HJ
D001881:Borates / Q000138:chemical synthesis; D003500:Cyclization; D034261:Epothilones / Q000138:chemical synthesis; D004852:Epoxy Compounds / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D043823:Taxoids / Q000138:chemical synthesis
D001881:Borates; D034261:Epothilones; D004852:Epoxy Compounds; D018942:Macrolides; D043823:Taxoids; C117305:laulimalide; C092170:tartrolon B; C093788:epothilone B