Synthesis of viridiofungin A trimethyl ester and determination of the absolute structure of viridiofungin A

被引:26
作者
Esumi, T [1 ]
Iwabuchi, Y [1 ]
Irie, H [1 ]
Hatakeyama, S [1 ]
机构
[1] Nagasaki Univ, Fac Pharmaceut Sci, Nagasaki 852, Japan
关键词
D O I
10.1016/S0040-4039(97)10754-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Four diastereoisomeric trimethyl esters of viridiofungin A, a member of novel family of aminoacyl alkyl citrate compounds, were synthesized in a highly stereoselective manner and the absolute configuration of natural viridiofungin A was determined to be 3S,4S,2'S. (C) 1998 Elsevier Science Ltd. All rights reserved.
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收藏
页码:877 / 880
页数:4
相关论文
共 10 条
[1]   INHIBITORS OF SQUALENE BIOSYNTHESIS AND METABOLISM [J].
ABE, I ;
TOMESCH, JC ;
WATTANASIN, S ;
PRESTWICH, GD .
NATURAL PRODUCT REPORTS, 1994, 11 (03) :279-302
[2]   (E)-3-(TRIMETHYLSILYL)-2-PROPEN-1-OL - AN IMPROVED PREPARATION [J].
DENMARK, SE ;
JONES, TK .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (23) :4595-4597
[3]   CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].
GAO, Y ;
HANSON, RM ;
KLUNDER, JM ;
KO, SY ;
MASAMUNE, H ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780
[4]   ISOLATION AND STRUCTURE ELUCIDATION OF VIRIDIOFUNGIN-A, VIRIDIOFUNGIN-B AND VIRIDIOFUNGIN-C [J].
HARRIS, GH ;
JONES, ETT ;
MEINZ, MS ;
NALLINOMSTEAD, M ;
HELMS, GL ;
BILLS, GF ;
ZINK, D ;
WILSON, KE .
TETRAHEDRON LETTERS, 1993, 34 (33) :5235-5238
[5]  
JOHNSON MR, 1979, TETRAHEDRON LETT, P4343
[6]   STRATEGY FOR THE SYNTHESIS OF LARGE PEPTIDES - AN APPLICATION TO THE TOTAL SYNTHESIS OF HUMAN PARATHYROID-HORMONE [HPTH(1-84)] [J].
KIMURA, T ;
TAKAI, M ;
MASUI, Y ;
MORIKAWA, T ;
SAKAKIBARA, S .
BIOPOLYMERS, 1981, 20 (09) :1823-1832
[7]   Viridiofungins, novel inhibitors of sphingolipid synthesis [J].
Mandala, SM ;
Thornton, RA ;
Frommer, BR ;
Dreikorn, S ;
Kurtz, MB .
JOURNAL OF ANTIBIOTICS, 1997, 50 (04) :339-343
[8]  
NADIN A, 1996, ANGEW CHEM INT EDIT, V35, P1622
[9]   Antimicrobial activity of viridiofungins [J].
Onishi, JC ;
Milligan, JA ;
Basilio, A ;
Bergstrom, J ;
Curotto, J ;
Huang, L ;
Meinz, M ;
NallinOmstead, M ;
Pelaez, F ;
Rew, D ;
Salvatore, M ;
Thompson, J ;
Vicente, F ;
Kurtz, MB .
JOURNAL OF ANTIBIOTICS, 1997, 50 (04) :334-338
[10]   COPPER(I)-CATALYZED REACTIONS OF BETA,GAMMA-EPOXY ALCOHOLS WITH GRIGNARD-REAGENTS [J].
TIUS, MA ;
FAUQ, AH .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4131-4132