Natural Products Containing the Oxetane and Related Moieties Present Additional Challenges for Structure Elucidation: A DU8+ Computational Case Study

被引：31

作者：

Kutateladze, Andrei G. ^{[1
]}

Holt, Tina ^{[1
]}

Reddy, D. Sai ^{[1
]}

机构：

[1] Univ Denver, Dept Chem & Biochem, Denver, CO 80208 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 12期

关键词：

PROTON COUPLING-CONSTANTS; CARBONYL-OLEFIN METATHESIS; ENDOPHYTIC FUNGUS; CHEMICAL-CONSTITUENTS; DICTYOTA-DICHOTOMA; H-1-NMR SPECTRA; NMR DATA; A-D; SESQUITERPENES; DERIVATIVES;

D O I：

10.1021/acs.joc.9b01005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Analysis of published NMR data for natural products containing the oxetane moiety, with the help of a recently developed parametric/DFT hybrid computational method DU8+, has revealed that oxetanes and related compounds constitute yet another significant challenge in structure elucidation and stereochemistry assignment, as more than 30 structures required revision. The most common pitfalls are discussed, and revised structures are suggested for 26 natural products.

引用

页码：7575 / 7586

页数：12

共 2 条

[1] DU8+Computations Reveal a Common Challenge in the Structure Assignment of Natural Products Containing a Carboxylic Anhydride Moiety
Novitskiy, Ivan M.
Kutateladze, Andrei G.
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (23): : 17511 - 17515
[2] THE CRYSTAL-STRUCTURE OF (S)-(-)-6-BROMO-5,7-DIHYDROXY-8-METHYL-2-PHENYL-2,3-DIHYDRO-4H-1-BENZOPYRAN-4-ONE [(-)-6-BROMOCRYPTOSTROBIN] AND A C-13 NMR-STUDY OF (+/-)-CRYPTOSTROBIN AND RELATED SUBSTANCES - REVISION OF THE STRUCTURES OF THE NATURAL-PRODUCTS (+/-)-LAWINAL, UNONAL, 7-0-METHYLUNONAL AND ISOUNONALD
BYRNE, LT
CANNON, JR
GAWAD, DH
JOSHI, BS
SKELTON, BW
TOIA, RF
WHITE, AH
AUSTRALIAN JOURNAL OF CHEMISTRY, 1982, 35 (09) : 1851 - 1858

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