EBC‐232 and 323: A Structural Conundrum Necessitating Unification of Five In Silico Prediction and Elucidation Methods. Issue 51 (30th August 2020)

• Record Type: Journal Article
• Authors: Maslovskaya, Lidia A.; Savchenko, Andrei I.; Krenske, Elizabeth H.; Chow, Sharon; Holt, Tina; Gordon, Victoria A.; Reddell, Paul W.; Pierce, Carly J.; Parsons, Peter G.; Boyle, Glen M.; Kutateladze, Andrei G.; Williams, Craig M.
• Is Part Of: Chemistry. Volume 26:Issue 51(2020)
• Page Start: 11862
• Page End: 11867
• Publication Date: 2020-08-30
• Subjects: Australian rainforest -- DP4 -- DU8+ -- EBC -- halimane -- in silico; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202001884
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Abstract : Solve me if you can : Structurally unique halimanes EBC‐232 and 323 invoked deployment of no less than 4 in silico NMR elucidation and prediction methods to arrive at two structures that also met chemical observations of interconversion.