Development of Novel Routes and Methods for the Semisynthesis of the Marine Steroid Demethylgorgosterol and Unnatural Analogs (Paperback) (ISBN-13: 9783832555160)

Gorgosterol and its derivative demethylgorgosterol are two long known marine steroids with unusual properties and a unique structure, containing a cyclopropane moiety in the side chain. Gorgosterol and its derivatives show diverse structural motives and biological activities. Moreover, corals and coral reefs have a tremendous ecological and economic impact but are endangered by climate change. A better understanding of corals can therefore aid their protection and conservation. 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.

Author: Nicolai Rosenbaum
ISBN-10: 3832555161
ISBN-13: 9783832555160
Publisher: Logos Verlag Berlin
Language: English
Published: 07/29/2022
Pages: 299
Format: Paperback
Weight: 14.28lbs