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Vol. 28 No. 4 (2016): Vol 28 Issue 4

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Total Synthesis of S (+)-Curcuphenol, S (+)-Curcuquinone and S (+)-Curcuhydroquinone

https://doi.org/10.14233/ajchem.2016.19475
Ramakoteswara Rao Chinta
Evolva Biotech Private Limited, TICEL Bio Park Limited, Taramani, Chennai-600 113, India
V. Harikrishna
Department of Chemistry, JNTUH College of Engineering, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, Hyderabad-500 085, India
Vijaya Kumar Tulam
Evolva Biotech Private Limited, TICEL Bio Park Limited, Taramani, Chennai-600 113, India
Naveen Kumar Bejjanki
Evolva Biotech Private Limited, TICEL Bio Park Limited, Taramani, Chennai-600 113, India
Prathama S. Mainkar
Evolva Biotech Private Limited, TICEL Bio Park Limited, Taramani, Chennai-600 113, India
P.K. Dubey
Department of Chemistry, JNTUH College of Engineering, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, Hyderabad-500 085, India

Corresponding Author(s) : Ramakoteswara Rao Chinta

rkrao983@gmail.com

Asian Journal of Chemistry, Vol. 28 No. 4 (2016): Vol 28 Issue 4

Abstract

A synthesis of (-)-curcuphenol, (-)-curcuquinone and (-)-curcuhydroquinone from o-valerolactone is described. The key steps include an Evans asymmetric methylation of 5-(benzyloxy)pentanoic acid (5), an oxidative aromatization of enone (11) and a regioselective oxidation of the phenol to o-quinone derivative with bis(trifluoro acetate)iodobenzene.

Keywords

Evans asymmetric methylation Robinson annulation [1,3]-Oxidative rearrangement
Chinta, R. R., Harikrishna, V., Tulam, V. K., Bejjanki, N. K., Mainkar, P. S., & Dubey, P. (2015). Total Synthesis of S (+)-Curcuphenol, S (+)-Curcuquinone and S (+)-Curcuhydroquinone. Asian Journal of Chemistry, 28(4), 771–778. https://doi.org/10.14233/ajchem.2016.19475
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