0000000000890067
AUTHOR
Nora M. Kaluza
Total Synthesis of (-)-C/D-cis-Dehydro-3-O-methyl-estradiols
A convergent synthesis of (–)-dehydro-3-O-methyl-C/D-cis-estradiol started from stereochemically defined substituted optically active 3-(2-arylethyl)-γ-butyrolactones. Regioselective bromination of the anisyl moiety, reductive ring opening of the iodolactone, and protecting-group changes led to a Weinreb amide. This then underwent an intramolecular Grignard reaction closing the B-ring to give a tetralone with defined configuration. Introduction of C-11 through an allyl Grignard addition and subsequent ring-closing metathesis gave a tetrahydro phenanthrene derivative. Oxidation of the side-chain alcohol resulted in the key aldehyde group, and a final samarium-diiodide-mediated reductive D-ri…
CCDC 1428732: Experimental Crystal Structure Determination
Related Article: Nora M. Kaluza, Dieter Schollmeyer, Udo Nubbemeyer|2016|Eur.J.Org.Chem.|2016|357|doi:10.1002/ejoc.201501341
CCDC 1428734: Experimental Crystal Structure Determination
Related Article: Nora M. Kaluza, Dieter Schollmeyer, Udo Nubbemeyer|2016|Eur.J.Org.Chem.|2016|357|doi:10.1002/ejoc.201501341
CCDC 1428733: Experimental Crystal Structure Determination
Related Article: Nora M. Kaluza, Dieter Schollmeyer, Udo Nubbemeyer|2016|Eur.J.Org.Chem.|2016|357|doi:10.1002/ejoc.201501341