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

Microsoft Word
mmc1.doc - Supplemental Material
Restricted to Registered users only
Download (5MB) | Request a copy

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.

[error in script]

IITH Creators:

IITH Creators	ORCiD
Khan, Faiz Ahmed	UNSPECIFIED

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