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Synlett 2013; 24(5): 535-549
DOI: 10.1055/s-0032-1318217
DOI: 10.1055/s-0032-1318217
account
Computational Chemistry; A Useful Tool for the Chemical Synthesis of Complex Molecules, Heterocycles and Catalysts
Further Information
Publication History
Received: 17 December 2012
Accepted after revision: 22 January 2013
Publication Date:
12 February 2013 (online)
Abstract
This Account describes our recent studies on the chemical synthesis of cyclic, densely substituted molecules by means of a hybrid approach consisting of the synergistic interaction between computational and experimental chemistry. In addition, two related total syntheses of complex molecules (±)-Scopadulin and (–)-Exiguolide are presented as case studies in which computational chemistry can be used to detect and, eventually, avoid potential failures involving key transformations of advanced intermediates.
1 Introduction
2 Computational Treatment of Molecules
3 Computational Characterization of Reactants, Reaction Intermediates, Products and Transition Structures
4 Computational–Experimental Analysis of the Stereocontrol in Thermal Pericyclic Reactions
4.1 Concerted and Stepwise [3+2] Cycloadditions
4.2 Concerted and Stepwise [8+2] Cycloadditions
5 Total Synthesis of Complex Molecules; Two Case Studies
5.1 Total Synthesis of (±)-Scopadulin
5.2 Total Synthesis of (–)-Exiguolide
6 Conclusions and Outlook
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