Research Catalog

Title

Development of Novel Routes and Methods for the Semisynthesis of the Marine Steroid Demethylgorgosterol and Unnatural Analogs / Nicolai Rosenbaum.

Author

Rosenbaum, Nicolai

Publication

Berlin : Logos Verlag, [2022]

Items in the Library & Off-site

Details

Description

xvii, 276 pages : illustrations; 21 cm.

Series Statement

Beiträge zur organischen Synthese, 1862-5681 ; Band 97

Uniform Title

Beiträge zur organischen Synthese ; Band 97.

Subject

• Sterols
• Biosynthesis

Note

• Published version of author's academic dissertation, from Karlsruher Institut für Technologie.

Bibliography (note)

• Includes bibliographical references.

Language (note)

• In English. Series, Title page and Abstract in English and German.

Contents

1 Introduction -- 1.1 Steroids[11] -- 1.1.1 Introduction -- 1.1.2 Biosynthesis -- 1.1.3 Importance for Nature and Medicine -- 1.2 Gorgosterol -- 1.2.1 Introduction[11,26] -- 1.2.2 Previous Semisyntheses -- 1.2.3 Previous work in our group -- 2 Aim of this work -- 3 Results and discussion -- 3.1 Towards a new semisynthesis of demethylgorgosterol and gorgosterol -- 3.1.1 Synthesis of the steroidal alkene -- 3.1.2 Stereoselective cyclopropanation[26] -- 3.1.3 Formal semisynthesis of demethylgorgosterol[26] -- 3.1.4 Comparison to previous syntheses[26] -- 3.1.5 Further work on demethylgorgosterol and gorgosterol -- 3.2 Synthesis of demethylgorgosterol analogs -- 3.2.1 Hydrocarbon analogs -- 3.2.2 Functionalized analogs -- 3.2.3 Double cyclopropanated analogs -- 3.2.4 Fluorophore-steroid conjugates -- 3.3 3-Cyclopropylacrylates by cyclopropanation using a vinylogous diazoester -- 3.3.1 Introduction -- 3.3.2 Optimization of the reaction conditions -- 3.3.3 Scope and limitations of the cyclopropanation and a plausible mechanism -- 3.3.4 Follow-up chemistry of the cyclopropylacrylates -- 3.3.5 Unexpected selectivity with 9-vinylanthracene -- 3.3.6 Synthesis of a new paracyclophane-based ligand -- 4 Summary and outlook -- 4.1 Development of a new semisynthesis of demethylgorgosterol and gorgosterol[26] -- 4.2 Synthesis of demethylgorgosterol analogs -- 4.3 3-Cyclopropylacrylates by cyclopropanation using a vinylogous diazo ester -- 5 Experimental -- 5.1 General information -- 5.1.1 Solvents, reagents, and methods -- 5.1.2 Analytical devices and instruments -- 5.2 Synthetic methods and characterization data -- 5.2.1 General procedures -- 5.2.2 Synthetic Methods and Characterization Data for Chapter 3.1 -- 5.2.3 Synthetic Methods and Characterization Data for Chapter 3.2 -- 5.2.4 Synthetic Methods and Characterization Data for Chapter 3.2 -- 5.3 Crystallographic data -- 5.3.1 Crystallographic Data Solved by Dr. Olaf Fuhr -- 5.3.2 Crystallographic Data Solved by Dr. Martin Nieger -- 6 References -- 7 Appendix -- 7.1 List of abbreviations and acronyms -- 7.2 Curriculum vitae -- 7.3 List of publications -- 7.4 Acknowledgments

ISBN

• 3832555161
• 9783832555160
• 9783832584597 (canceled/invalid)
• 3832584595 (canceled/invalid)

LCCN

99993394519

OCLC

• on1350434290
• 1350434290
• SCSB-14465188

Owning Institutions

Columbia University Libraries