Absolute stereochemistry of TT-1 (rasfonin), an α-pyrone-containing natural product from a fungus, Trichurus terrophilus

被引:15
作者
Akiyama, K [1 ]
Kawamoto, S [1 ]
Fujimoto, H [1 ]
Ishibashi, M [1 ]
机构
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
关键词
D O I
10.1016/j.tetlet.2003.09.136
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The absolute stereochemistry of TT-1 (1 =rasfonin), an alpha-pyrone-containing natural product from a Fungi Imperfecti, Trichurus terrophilus, was determined as 5R,6R,7S,9R, and 6'S on the basis of synthesis of diastereomers of two fragments of 1 in optically active forms, and comparison of their spectral and optical data with those of natural specimens. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8427 / 8431
页数:5
相关论文
共 19 条
[1]  
AKIYAMA K, 2003, 123 ANN M PHARM SOC, P123
[3]   THE TOTAL SYNTHESES OF (+/-)-ALPHA-DIHYDROCLEAVAMINES AND BETA-DIHYDROCLEAVAMINES, (+/-)-16-METHOXYCARBONYLDIHYDROCLEAVAMINE, (+/-)-CORONARIDINE, (+/-)-DIHYDROCATHARANTHINE, (+/-)-IBOGAMINE, (+/-)-EPI-IBOGAMINE AND (+/-)-CATHARANTHINE [J].
ATTAURRAHMAN ;
BEISLER, JA ;
HARLEYMASON, J .
TETRAHEDRON, 1980, 36 (08) :1063-1070
[4]  
DORMAN DE, 1971, J ORG CHEM, V36, P2757
[5]  
FUJIMOTO H, 2000, 120 ANN M PHARM SOC, P68
[6]  
Fujita K, 2001, EUR J ORG CHEM, V2001, P493, DOI 10.1002/1099-0690(200102)2001:3<493::AID-EJOC493>3.0.CO
[7]  
2-B
[8]   FACILE ACCESS TO (S)-1,2,4-BUTANETRIOL AND ITS DERIVATIVES [J].
HANESSIAN, S ;
UGOLINI, A ;
DUBE, D ;
GLAMYAN, A .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (11) :2146-2147
[9]   Absolute configuration of aflastatin A, a specific inhibitor of aflatoxin production by Aspergillus parasiticus [J].
Ikeda, H ;
Matsumori, N ;
Ono, M ;
Suzuki, A ;
Isogai, A ;
Nagasawa, H ;
Sakuda, S .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (02) :438-444
[10]   Studies on the stereochemistry of theonezolides A-C1:: Elucidation of the relative configurations of 1,3-diol moieties of the C-4∼C-17 fragment [J].
Kobayashi, J ;
Yonezawa, M ;
Takeuchi, S ;
Ishibashi, M .
HETEROCYCLES, 1998, 49 :39-42