Total synthesis of proposed elgonene C and its (4R,5R)-diastereomer
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Updated: Oct 1, 2025

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
Sudip Mandal1, Barla Thirupathi1
1Department of Chemical Sciences, Indian Institute of Science Education and Research Berhampur, Transit Campus, Govt. ITI Building, NH 59, Engineering School Road, Ganjam-District, Berhampur 760 010, Odisha, India. thirupathibarla@iiserbpr.ac.in.
Abstract:
The total synthesis of the proposed elgonene C (1) and its (4R,5R)-diastereomer (1a) has been achieved using a second-generation oxazaborolidinium ion-catalysed Diels-Alder reaction, Sharpless asymmetric dihydroxylation, and a Ni-catalysed cross-carboxyl coupling reaction via redox-active ester (RAE) formation as key reactions. The spectral and analytical data for our synthetic compounds 1 and 1a do not match the isolation data provided by Stadler et al. which indicates that structural revision is required for the proposed elgonene C.
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