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Literature DB >> 16774284

Predicting NMR spectra by computational methods: structure revision of hexacyclinol.

Abstract

[structure: see text] The structure of the natural product hexacyclinol was reassigned from endoperoxide 1 to the diepoxide 7 on the basis of calculated (13)C chemical shift data using HF/3-21G geometries and mPW1PW91/6-31G(d,p) GIAO NMR predictions. These predictions correlate very well with experimental data for three other highly oxygenated natural products, elisapterosin B, maoecrystal V, and elisabethin A. Hexacyclinol is proposed to arise from acid-catalyzed rearrangement of panepophenanthrin in the presence of methanol.

Entities: Chemical

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Year: 2006 PMID： 16774284 DOI： 10.1021/ol0611346

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

26 in total

1. A distinctive structural twist in the aminoimidazole alkaloids from a calcareous marine sponge: isolation and characterization of leucosolenamines A and B.

Authors: Paul Ralifo; Karen Tenney; Frederick A Valeriote; Phillip Crews
Journal: J Nat Prod Date: 2007-01 Impact factor: 4.050

2. Structural determination of complex natural products by quantum mechanical calculations of (13)C NMR chemical shifts: development of a parameterized protocol for terpenes.

Authors: Ana Carolina Ferreira de Albuquerque; Daniel Joras Ribeiro; Mauro Barbosa de Amorim
Journal: J Mol Model Date: 2016-07-16 Impact factor: 1.810

10. Effect of conformational rigidity on the stereoselectivity of nucleophilic additions to five-membered ring bicyclic oxocarbenium ion intermediates.

Authors: Olga Lavinda; Vi Tuong Tran; K A Woerpel
Journal: Org Biomol Chem Date: 2014-09-28 Impact factor: 3.876

Predicting NMR spectra by computational methods: structure revision of hexacyclinol.

1. A distinctive structural twist in the aminoimidazole alkaloids from a calcareous marine sponge: isolation and characterization of leucosolenamines A and B.

2. Structural determination of complex natural products by quantum mechanical calculations of (13)C NMR chemical shifts: development of a parameterized protocol for terpenes.

3. Asymmetric transformations of achiral 2,5-cyclohexadienones.

4. Stereochemical revision of xylogranatin F by GIAO and DU8+ NMR calculations.

5. A guide to small-molecule structure assignment through computation of (¹H and ¹³C) NMR chemical shifts.

6. Questions in natural products synthesis research that can (and cannot) be answered using computational chemistry.

7. (+)-hexacyclinol.

8. Computer-assisted methods for molecular structure elucidation: realizing a spectroscopist's dream.

9. Structure revision of spiroleucettadine, a sponge alkaloid with a bicyclic core meager in H-atoms.

10. Effect of conformational rigidity on the stereoselectivity of nucleophilic additions to five-membered ring bicyclic oxocarbenium ion intermediates.