Abstract
The D3-trishomocubane is a unique high symmetrical chiral stabilomeric compound. Its derivatives have great potential to be used as scaffolds for drugs, in structure-oriented design, asymmetric catalysis, light-driven systems and much more. Axial substitution is the most useful method for this purpose but the least studied. This paper critically analyzes various synthetic strategies aiming at introducing substituents into C2/C9 positions of D3-trishomocubane. Herein we cover formation of trishomocubane skeleton and rearrangement of Cs-trishomocubanes. Based on a comprehensive retrosynthetic analysis a general synthetic scheme is proposed.
Keywords: Cs-trishomocubane, D3-trishomocubane, tertiary derivatives, axial derivatives, retrosynthetic analysis, cyclopentadienes, quinones
Current Organic Chemistry
Title:Axial D3-trishomocubane Derivatives with Potential: Dreams or Reality?
Volume: 16 Issue: 22
Author(s): Dmitry I. Sharapa, Igor A. Levandovskiy and Tatyana E. Shubina
Affiliation:
Keywords: Cs-trishomocubane, D3-trishomocubane, tertiary derivatives, axial derivatives, retrosynthetic analysis, cyclopentadienes, quinones
Abstract: The D3-trishomocubane is a unique high symmetrical chiral stabilomeric compound. Its derivatives have great potential to be used as scaffolds for drugs, in structure-oriented design, asymmetric catalysis, light-driven systems and much more. Axial substitution is the most useful method for this purpose but the least studied. This paper critically analyzes various synthetic strategies aiming at introducing substituents into C2/C9 positions of D3-trishomocubane. Herein we cover formation of trishomocubane skeleton and rearrangement of Cs-trishomocubanes. Based on a comprehensive retrosynthetic analysis a general synthetic scheme is proposed.
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Cite this article as:
I. Sharapa Dmitry, A. Levandovskiy Igor and E. Shubina Tatyana, Axial D3-trishomocubane Derivatives with Potential: Dreams or Reality?, Current Organic Chemistry 2012; 16 (22) . https://dx.doi.org/10.2174/138527212804004508
DOI https://dx.doi.org/10.2174/138527212804004508 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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