EBC-232 and 323: A Structural Conundrum Necessitating Unification of Five In Silico Prediction and Elucidation Methods.
Lidia A MaslovskayaAndrei I SavchenkoElizabeth H KrenskeSharon ChowTina HoltVictoria A GordonPaul W ReddellCarly J PiercePeter G ParsonsGlen M BoyleAndrei G KutateladzeCraig M WilliamsPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2020)
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.