Development of Novel Routes and Methods for the Semisynthesis of the Marine Steroid Demethylgorgosterol and Unnatural Analogs

By (author) Nicolai Rosenbaum

Book cover: Development of Novel Routes and Methods for the Semisynthesis of the Marine Steroid Demethylgorgosterol and Unnatural Analogs

Extent: 299, 299 pages

Publisher: Logos Verlag Berlin

Subjects: Earth & Life Sciences 

Series: Beiträge zur organischen Synthese

Series volume number: 97

Language: English

Paperback (Published)

(July 2022)

ISBN: 9783832555160

5.71 x 8.27 inches

Price: $76.00

Out of stock

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.

  • By (author) Nicolai Rosenbaum

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