Synthesis 2021; 53(03): 475-488
DOI: 10.1055/s-0040-1705953
short review

Synthesis of Cyclohexane-Angularly-Fused Triquinanes

a  Department of Chemistry, University of Pennsylvania, 231 S. 34th Street, Philadelphia, PA 19104-6323, USA   Email: [email protected]   Email: [email protected]
b  Therapeutics and Biotechnology Division, Korea Research Institute of Chemical Technology, Daejeon, 34114, Korea   Email: [email protected]
,
Jeffrey D. Winkler
a  Department of Chemistry, University of Pennsylvania, 231 S. 34th Street, Philadelphia, PA 19104-6323, USA   Email: [email protected]   Email: [email protected]
› Author Affiliations
We would like to thank the National Institutes of Health (P01-CA025874), the Petroleum Research Fund, administered by the American Chemical Society, and the University of Pennsylvania for financial support.


Dedicated with great affection, admiration and gratitude to Professor Madeleine M. Joullié, who has inspired generations of synthetic chemists with her passion for science, her intellectual rigor and her warmth and humor.

Abstract

Cyclohexane-angularly-fused triquinanes, 6-5-5-5 tetra­cycles, have attracted the attention of synthetic chemists due to their highly congested core structures and multiple quaternary carbon centers. This review focuses on the six completed total synthesis of naturally occurring cyclohexane-angularly-fused triquinanes in addition to seven notable methodologies that have been developed for the synthesis of these structures.

1 Introduction

2 6-5-5-5 Tetracycles Containing a Linear Triquinane

2.1 Total Synthesis of Cyclopiane Diterpenes

2.2 Synthetic Approach toward Aberrarane Diterpenes

2.3 Intermediates in the Total Synthesis of Magellanine-Type Alkaloids

3 6-5-5-5 Tetracycles Containing an Angular Triquinane

3.1 Total Synthesis of Waihoensene

3.2 Miscellaneous Approaches

4 Conclusion



Publication History

Received: 16 July 2020

Accepted after revision: 24 August 2020

Publication Date:
03 November 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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