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Synlett 2023; 34(15): 1752-1764
DOI: 10.1055/a-2039-6440
DOI: 10.1055/a-2039-6440
account
Lessons from the Total Synthesis of Highly Substituted Benzophenone Natural Products
We gratefully acknowledge initial funding of the work on mumbaistatin by Sanofi-Aventis. We thank the Universität zu Köln (University of Cologne) and the Fond der Chemischen Industrie for continuous support. The project was furthermore supported by postdoctoral fellowships to David Sucunca (from Comunidad Autónoma de La Rioja) and Dario Gerbino (from the Alexander von Humboldt-Stiftung), as well as doctoral stipends to Nikolay Slavov (from Evangelisches Studienwerk e.V. Villigst) and Lukas Münzer (Studienstiftung des Deutschen Volkes).
Dedicated to Prof. Franz-Peter Montforts on the occasion of his 75th birthday.
Abstract
In this account, we summarize the results and experience gained during 20 years of research in the field of polyketidic natural products displaying a tetra-ortho-substituted benzophenone substructure. As demonstrated by the various approaches towards mumbaistatin and pestalone as targets of high biological relevance, the synthesis of such systems is surprisingly difficult due to the intense interactions of the functional groups adjacent to the ketone bridge. We report successes and failures, as well as the discovery of surprising reactivities that are important for understanding the non-enzymatic formation of related compounds in Nature.
1 Introduction
2 Mumbaistatin
3 Pestalone
4 Conclusion
Key words
benzophenones - mumbaistatin - pestalone - phthalides - isoindolinones - carbonyl–olefin metathesis - coupling reactionsPublication History
Received: 14 February 2023
Accepted: 21 February 2023
Accepted Manuscript online:
21 February 2023
Article published online:
17 March 2023
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