Absolute configuration of the fungal metabolite spirolaxine

被引:23
作者
Bava, A
Clericuzio, M
Giannini, G
Malpezzi, L
Meille, SV
Nasini, G
机构
[1] CNR, ICRM, Dipartimento Chim Mat & Ingn Chim Politecn, I-20131 Milan, Italy
[2] Univ Turin, Dipartimento Chim Gen & Organ Applicata, I-10125 Turin, Italy
[3] Sigma Tau Pharmaceut Co, Res & Dev, I-00040 Pomezia, Italy
关键词
basidiomycetes; secondary metabolite; absolute configuration; circular dichroism; angiogenesis; spiro compounds;
D O I
10.1002/ejoc.200400902
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The relative stereochemistry of the four stereocentres of spirolaxine 1, a bioactive 6,5-spiroacetal phthalide secondary metabolite, was determined through single-crystal X-ray analysis. Its absolute configuration was determined by circular dichroism; the experimental spectrum of spirolaxine is in good agreement with that evaluated by means of DeVoe coupled-oscillator calculations. (c) Wiley-VCH Verlag GmbH & Co.
引用
收藏
页码:2292 / 2296
页数:5
相关论文
共 21 条
[11]   USE OF CNDO METHOD IN SPECTROSCOPY .4. SMALL MOLECULES - SPECTRA AND GROUND-STATE PROPERTIES [J].
DELBENE, J ;
JAFFE, HH .
JOURNAL OF CHEMICAL PHYSICS, 1969, 50 (03) :1126-&
[13]  
DEWAR MJS, 1985, J AM CHEM SOC, V107, P3202
[14]   ON ENANTIOMORPH-POLARITY ESTIMATION [J].
FLACK, HD .
ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV) :876-881
[15]  
FRISCH MJ, 2001, GAUSSIAN 98 REVISION
[16]  
Giannini G., 2004, AACR ANN M ORL US 27
[17]  
Penco S., WO Pat., Patent No. [0168070, 01/68070]
[18]  
QUARONI S, COMMUNICATION
[19]  
ROSINI C, 1993, TETRAHEDRON-ASYMMETR, V4, P3199
[20]  
Sheldrick G.M., 1993, PROGRAM CRYSTAL STRU