Total synthesis of novel bioactive natural product paracaseolide A and analogues: Computational evaluation of a 'proposed' biomimetic Diels-Alder reaction

Vasamsetty, L and Sahu, D and Ganguly, B and Khan, Faiz Ahmed and Mehta, G (2014) Total synthesis of novel bioactive natural product paracaseolide A and analogues: Computational evaluation of a 'proposed' biomimetic Diels-Alder reaction. Tetrahedron, 70 (45). pp. 8488-8497. ISSN 0040-4020

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Abstract

A short and generally applicable synthesis of bioactive tetracyclic natural product paracaseolide A has been accomplished employing a 'proposed' biomimetic Diels-Alder reaction as the key strategic step. The Diels-Alder precursors for this purpose were readily assembled through a versatile Suzuki coupling on preformed α-halo butenolides. The mechanistic aspects of the 'putative' biomimetic Diels-Alder reaction have been probed using computational methods, which suggest that this [4+2]-cycloaddition proceeds through a step-wise process and product profile is thermodynamically governed.

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IITH Creators:
IITH CreatorsORCiD
Khan, Faiz AhmedUNSPECIFIED
Item Type: Article
Additional Information: L.V. and F.A.K. wish to thank the Council of Scientific and Industrial Research in India for the award of a Research Fellowship and research support, respectively. G.M. acknowledges the research support from Eli Lilly and Jubilant-Bhartia Foundations and the facilities extended by the University of Hyderabad.
Uncontrolled Keywords: Alkenyl butenolides; Diels-Alder dimerization; Gaussian 09 suite; Singlet oxygen; Suzuki coupling
Subjects: Chemistry
Divisions: Department of Chemistry
Depositing User: Team Library
Date Deposited: 24 Nov 2014 11:23
Last Modified: 21 Sep 2017 06:57
URI: http://raiith.iith.ac.in/id/eprint/927
Publisher URL: https://doi.org/10.1016/j.tet.2014.09.072
OA policy: http://www.sherpa.ac.uk/romeo/issn/0040-4020/
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