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NHC catalyzed enantioselective Coates-Claisen rearrangement : A rapid access to the dihydropyran core for Oleuropein based Secoiridoids

Abstract

We present a short synthesis of a suitably functionalized enantioselective dihydropyran core of Secoiridoids using N-heterocyclic carbene (NHC) catalyzed Coates-Claisen rearrangment mechanism. Key steps of the synthesis are (i) the highly enantioselective NHC catalyzed Coates-Claisen rearrangment for dihydropyran core (ii) the highly diastereoselective exocyclic trans alkene for the assembly of the target dihydropyran core structure of Oleuropein (iii) highly stereoselective assembly of monoterpene elenolide core structure

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Publication details

The article was received on 20 Oct 2017, accepted on 06 Dec 2017 and first published on 06 Dec 2017


Article type: Paper
DOI: 10.1039/C7NJ04057A
Citation: New J. Chem., 2017, Accepted Manuscript
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    NHC catalyzed enantioselective Coates-Claisen rearrangement : A rapid access to the dihydropyran core for Oleuropein based Secoiridoids

    S. vedachalam, N. Murugesh, P. Chakraborthy, R. Karvembu and X. Liu, New J. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7NJ04057A

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