Buch, Englisch, Band 97, 299 Seiten, PB, Format (B × H): 145 mm x 210 mm
Buch, Englisch, Band 97, 299 Seiten, PB, Format (B × H): 145 mm x 210 mm
Reihe: Beiträge zur organischen Synthese
ISBN: 978-3-8325-5516-0
Verlag: Logos
A concise and high yielding formal semisynthesis for the marine steroid demethylgorgosterol was developed. Centerpiece was a stereoselective intermolecular cyclopropanation. A variety of demethylgorgosterol analogs were synthesized for biological applications. These include hydrocarbon analogs, diversely functionalized analogs, and fluorophore-steroid conjugates to track and visualize steroids in vivo. Finally, a new method for the synthesis of 3-cyclopropylacrylates was developed. Here, a vinylogous diazoester was utilized to cyclopropanate alkenes. The observed cis-selectivity was explained with p-p-interactions in the transition state.