Configurational analysis of the natural product passifloricin A by quantum mechanical 13C NMR GIAO chemical shift calculations

被引：28

作者：

Bifulco, G ^{[1
]}

Gomez-Paloma, L ^{[1
]}

Riccio, R ^{[1
]}

机构：

[1] Univ Salerno, Dipartimento Sci Farmaceut, I-84084 Salerno, Italy

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 38期

关键词：

GIAO; 13C NMR; DFT calculations; natural products; passifloricin; configurational analysis;

D O I：

10.1016/S0040-4039(03)01810-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Quantum chemical calculations at mPW1PW91 level, with full geometry optimization, using the 6-31 g(d) basis set, and GIAO (gauge including atomic orbitals) C-13 NMR chemical shifts using the 6-31g(d,p) basis set, are here utilized as a support to define the configurational features of the natural product passifloricin A, whose previously proposed relative configuration has been recently shown, by synthetic studies. to be incorrect. This study suggests that the relative stereostructure for passifloricin A corresponds to the delta-lactone of the (5R,7R,9S,11R)-tetrahydroxyhexttcos-2-enoic acid. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：7137 / 7141

页数：5

共 11 条

[1] Exchange functionals with improved long-range behavior and adiabatic connection methods without adjustable parameters:: The mPW and mPW1PW models [J].