Addressing the Challenges of Structure Elucidation in Natural Products Possessing the Oxirane Moiety | Zendy

Andrei G. Kutateladze | Zendy; Dmitry M. Kuznetsov | Zendy; Anastasia A. Beloglazkina | Zendy; Tina Holt | Zendy

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Addressing the Challenges of Structure Elucidation in Natural Products Possessing the Oxirane Moiety

Author(s) -

Andrei G. Kutateladze,

Dmitry M. Kuznetsov,

Anastasia A. Beloglazkina,

Tina Holt

Publication year - 2018

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.8b01027

Subject(s) - moiety , stereochemistry , chemistry , molecule , combinatorial chemistry , organic chemistry

NMR data for natural products containing the epoxy moiety have been revisited and reanalyzed with the help of a recently developed parametric/DFT hybrid computational method, DU8+. More than 20 structures needed revision, which points to challenges in NMR solution structure assignment for molecules possessing this structural feature. Among the revised structures are achicretin 2, acremine P, aromaticane I, artanomalide B, botryosphaerihydrofuran, chloroklotzchin, crithmifolide, crotodichogamoin A, emervaridone C, 9α,15-epoxyafricanane, fischambiguine B, grandilobalide B, guaianolide A, guatterfriesols A and B, juncenolide G, roscotane D, secoafricane 7, taccalonolides AJ and AF, and related compounds.

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