EBC-232 and 323: A Structural Conundrum Necessitating Unification of Five In Silico Prediction and Elucidation Methods

Lidia A Maslovskaya; Andrei I Savchenko; Elizabeth H Krenske; Sharon Chow; Tina Holt; Victoria A Gordon; Paul W Reddell; Carly J Pierce; Peter G Parsons; Glen M Boyle; Andrei G Kutateladze; Craig M Williams

doi:10.1002/chem.202001884

EBC-232 and 323: A Structural Conundrum Necessitating Unification of Five In Silico Prediction and Elucidation Methods

Chemistry. 2020 Sep 10;26(51):11862-11867. doi: 10.1002/chem.202001884. Epub 2020 Aug 30.

Affiliations

¹ School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, 4072, Australia.
² QIMR Berghofer Medical Research Institute, PO Royal Brisbane Hospital, Brisbane, 4029, Australia.
³ Department of Chemistry and Biochemistry, University of Denver, Denver, CO, 80208, USA.
⁴ EcoBiotics Limited, PO Box 1, Yungaburra, 4884, Queensland, Australia.

PMID: 32864777
DOI: 10.1002/chem.202001884

Abstract

Structurally unique halimanes EBC-232 and EBC-323, isolated from the Australian rainforest plant Croton insularis, proved considerably difficult to elucidate. The two diastereomers, which consist an unusual oxo-6,7-spiro ring system fused to a dihydrofuran, were solved by unification and consultation of five in silico NMR elucidation and prediction methods [i.e., ACDLabs, olefin strain energy (OSE), DP4, DU8+ and TD DFT CD]. Structure elucidation challenges of this nature are prime test case examples for empowering future AI learning in structure elucidation.

Keywords: Australian rainforest; DP4; DU8+; EBC; halimane; in silico.

Grants and funding

University of Queensland