Synlett 2021; 32(02): 119-139
DOI: 10.1055/s-0040-1707226
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© Georg Thieme Verlag Stuttgart · New York

Adventures and Detours in the Synthesis of Hydropentalenes

Max Deimling
a  Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany   Email: sabine.laschat@oc.uni-stuttgart.de
,
Anna Zens
a  Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany   Email: sabine.laschat@oc.uni-stuttgart.de
,
Natja Park
a  Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany   Email: sabine.laschat@oc.uni-stuttgart.de
,
Christine Hess
a  Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany   Email: sabine.laschat@oc.uni-stuttgart.de
,
Simon Klenk
a  Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany   Email: sabine.laschat@oc.uni-stuttgart.de
,
Zarfishan Dilruba
a  Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany   Email: sabine.laschat@oc.uni-stuttgart.de
b  Department of Chemistry, University of Leicester, University Road, Leicester, LE1 7RH, UK
,
Angelika Baro
a  Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany   Email: sabine.laschat@oc.uni-stuttgart.de
,
a  Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany   Email: sabine.laschat@oc.uni-stuttgart.de
› Author Affiliations
Generous financial support by the Deutsche Forschungsgemeinschaft (DFG, project number 358283783 - SFB 1333, subproject B3), the Ministerium für Wissenschaft, Forschung und Kunst des Landes Baden-Württemberg, the Fonds der Chemischen Industrie and the European Commission (ERASMUS fellowship for Z.D.) is gratefully acknowledged.
Further Information

Publication History

Received: 16 June 2020

Accepted after revision: 30 June 2020

Publication Date:
18 August 2020 (online)


◊ These coauthors contributed equally to this work.

Abstract

Functionalized hydropentalenes (i.e., bicyclo[3.3.0]octanones) constitute important building blocks for natural products and for ligands for asymmetric catalysis. The assembly and tailored functionalization of this convex roof-shaped scaffold is challenging and has motivated a variety of synthetic approaches including our own contributions, which will be presented in this account.

1 Introduction

2 Biosynthesis of Hydropentalenes

3 Hydropentalenes through the Pauson–Khand Reaction

4 Hydropentalenes through Transannular Oxidative Cyclization of Cycloocta-1,4-diene

5 Functionalization of Bicyclo[3.3.0]octan-1,4-dione to Dodecahydrocyclopenta[a]indenes

6 Functionalization of Bicyclo[3.3.0]octan-1,4-diones to Crown Ether Hybrids

7 Functionalization of Bicyclo[3.3.0]octan-1,4-dione to Cylindramide

8 Tandem Ring-Opening Metathesis/Ring-Closing Metathesis/Cross-Metathesis of Bicyclo[2.2.1]heptanes

9 Functionalization of Bicyclo[3.3.0]octan-1,4-dione to Geodin A

10 Hydropentalenes through Enantioselective Desymmetrization of Weiss Diketones

11 Functionalization of Weiss Diketones by Carbonyl Ene Reactions

12 Functionalization of the Weiss Diketone to Cylindramide and Geodin A Core Units

13 Biological Properties of Bicyclo[3.3.0]octanes

14 Hydropentalenes through Vinylcyclopropane Cyclopentene Rearrangement

15 Functionalization of Bicyclo[3.3.0]octanes toward Chiral Dienes

16 Miscellaneous Syntheses of Hydropentalenes

17 Conclusion and Outlook

Supporting Information

 
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