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Title: Cyclization Strategies for the Concurrent Installation of Multiple Quaternary Stereogenic Centers
Abstract

In this review we highlight the general cyclization strategies currently available to organic chemists for the concurrent and stereoselective installation of multipleQuaternary Stereogenic Centers(QSC) atoms in cyclic or polycyclic architectures. QSCs embedded in rigid cyclic architectures are motifs found in many blockbuster drugs and important bioactive natural product classes, and yet, direct access to these structures stereoselectively from simple precursors remains a significant challenge. Underscoring the difficulty associated with their synthesis, such topologically three‐dimensional molecules are underrepresented in existing small molecule compound libraries, which are instead dominated by linear or flat molecules. This review focuses on methods disclosed in both natural product synthesis and methodology studies since the turn of the 21stcentury. The cases to be examined successfully achieve these challenging transformations: (1)one‐step assembly of the cyclized architecture; and (2)concurrent stereoselective installation of multiple (≥2) new QSCs. These cyclization strategies, which address the aforementioned fundamental challenges in complex molecule synthesis, have been categorized into five broad groups: i) Biomimetic Polyene Cyclization Cascades; ii) Cyclization Cascades of Prochiral Alkenes; iii) Cycloadditions; iv) Dearomatizations; v) Electrocyclizations.

 
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Award ID(s):
1900050
NSF-PAR ID:
10449907
Author(s) / Creator(s):
 ;  
Publisher / Repository:
Wiley Blackwell (John Wiley & Sons)
Date Published:
Journal Name:
Israel Journal of Chemistry
Volume:
61
Issue:
7-8
ISSN:
0021-2148
Page Range / eLocation ID:
p. 469-485
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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