Predicting NMR spectra by computational methods: Structure revision of hexacyclinol

被引：159

作者：

Rychnovsky, Scott D. ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 13期

关键词：

D O I：

10.1021/ol0611346

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The structure of the natural product hexacyclinol was reassigned from endoperoxide 1 to the diepoxide 7 on the basis of calculated C-13 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.

引用

页码：2895 / 2898

页数：4

共 21 条

[1]

Bagno A, 2001, CHEM-EUR J, V7, P1652, DOI 10.1002/1521-3765(20010417)7:8<1652::AID-CHEM16520>3.3.CO

[2]

2-M

[3]

Barone G, 2002, CHEM-EUR J, V8, P3233, DOI 10.1002/1521-3765(20020715)8:14<3233::AID-CHEM3233>3.0.CO

[4]

2-0

[5]

Barone G, 2002, CHEM-EUR J, V8, P3240, DOI 10.1002/1521-3765(20020715)8:14<3240::AID-CHEM3240>3.0.CO

[6]

2-G

[7] Quantum mechanical calculations of NMR J coupling values in the determination of relative configuration in organic compounds [J].

Bifulco, G ;

Bassarello, C ;

Riccio, R ;

Gomez-Paloma, L .

ORGANIC LETTERS, 2004, 6 (06) :1025-1028

[8] Comparison of different theory models and basis sets in the calculation of 13C NMR chemical shifts of natural products [J].

Cimino, P ;

Gomez-Paloma, L ;

Duca, D ;

Riccio, R ;

Bifulco, G .

MAGNETIC RESONANCE IN CHEMISTRY, 2004, 42 :S26-S33

[9] Computed C-13 NMR chemical shifts via empirically scaled GIAO shieldings and molecular mechanics geometries. Conformation and configuration from C-13 shifts [J].

Forsyth, DA ;

Sebag, AB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (40) :9483-9494

[10] RETRACTED: Total syntheses of hexacyclinol, 5-epi-hexacycyclinol, and desoxohexacyclinol unveil an antimalarial prodrug motif (Retracted article. See vol. 51, pg. 2769, 2012) [J].

La Clair, JF .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (17) :2769-2773

← 1 2 3 →