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Issue 3, 2018
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NHC catalyzed enantioselective Coates-Claisen rearrangement: a rapid access to the dihydropyran core for oleuropein based secoiridoids

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Abstract

We present the short synthesis of the suitably functionalized enantioselective dihydropyran core of secoiridoids using an N-heterocyclic carbene (NHC) catalyzed Coates-Claisen rearrangement mechanism. The key steps of the synthesis are (i) the highly enantioselective NHC catalyzed Coates-Claisen rearrangement for the dihydropyran core, (ii) the assembly of the target dihydropyran core structure of oleuropein from a highly diastereoselective exocyclic trans alkene, and (iii) the highly stereoselective assembly of a monoterpene elenolide core structure.

Graphical abstract: NHC catalyzed enantioselective Coates-Claisen rearrangement: a rapid access to the dihydropyran core for oleuropein based secoiridoids

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Article information


Submitted
20 Oct 2017
Accepted
06 Dec 2017
First published
06 Dec 2017

New J. Chem., 2018,42, 1832-1839
Article type
Paper

NHC catalyzed enantioselective Coates-Claisen rearrangement: a rapid access to the dihydropyran core for oleuropein based secoiridoids

S. Vedachalam, N. Murugesh, P. Chakraborty, R. Karvembu and X. Liu, New J. Chem., 2018, 42, 1832
DOI: 10.1039/C7NJ04057A

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