TY - JOUR
T1 - Total synthesis of novel bioactive natural product paracaseolide A and analogues
T2 - Computational evaluation of a 'proposed' biomimetic Diels-Alder reaction
AU - Vasamsetty, Laxmaiah
AU - Sahu, Debashis
AU - Ganguly, Bishwajit
AU - Khan, Faiz Ahmed
AU - Mehta, Goverdhan
N1 - Funding 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.
Publisher Copyright:
© 2014 Elsevier Ltd.
PY - 2014/11/11
Y1 - 2014/11/11
N2 - 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.
AB - 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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U2 - 10.1016/j.tet.2014.09.072
DO - 10.1016/j.tet.2014.09.072
M3 - Article
AN - SCOPUS:84907994634
SN - 0040-4020
VL - 70
SP - 8488
EP - 8497
JO - Tetrahedron
JF - Tetrahedron
IS - 45
ER -