Enantiospecific total synthesis of tryprostatin A

被引:29
作者
Gan, T [1 ]
Cook, JM [1 ]
机构
[1] UNIV WISCONSIN, DEPT CHEM, MILWAUKEE, WI 53201 USA
关键词
D O I
10.1016/S0040-4039(97)00077-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 3-methyl-6-methoxyindole 3 was converted into tryprostatin A (1) via a regiospecific bromination process coupled with the Schollkopf chiral auxiliary 7 to provide the 2-bromo-6-methoxy-tryptophan 8a as a key intermediate. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:1301 / 1304
页数:4
相关论文
共 15 条
[1]   ENTRY INTO 6-METHOXY-D(+)-TRYPTOPHANS - STEREOSPECIFIC SYNTHESIS OF 1-BENZENESULFONYL-6-METHOXY-D(+)-TRYPTOPHAN ETHYL-ESTER [J].
ALLEN, MS ;
HAMAKER, LK ;
LALOGGIA, AJ ;
COOK, JM .
SYNTHETIC COMMUNICATIONS, 1992, 22 (14) :2077-2102
[2]  
Bi Y., 1993, BIOACTIVE NATURAL A, V13
[3]   STEREOSELECTIVE SYNTHESIS OF DESMETHOXY-(+)-VERRUCULOGEN TR-2 [J].
BOYD, SA ;
THOMPSON, WJ .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (09) :1790-1794
[4]   Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus .2. Physico-chemical properties and structures [J].
Cui, CB ;
Kakeya, H ;
Osada, H .
JOURNAL OF ANTIBIOTICS, 1996, 49 (06) :534-540
[5]   Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus .1. Taxonomy, fermentation, isolation and biological properties [J].
Cui, CB ;
Kakeya, H ;
Okada, G ;
Onose, R ;
Osada, H .
JOURNAL OF ANTIBIOTICS, 1996, 49 (06) :527-533
[6]   TRYPROSTATIN-A AND TRYPROSTATIN-B, NOVEL MAMMALIAN-CELL CYCLE INHIBITORS PRODUCED BY ASPERGILLUS-FUMIGATUS [J].
CUI, CB ;
KAKEYA, H ;
OKADA, G ;
ONOSE, R ;
UBUKATA, M ;
TAKAHASHI, I ;
ISONO, K ;
OSADA, H .
JOURNAL OF ANTIBIOTICS, 1995, 48 (11) :1382-1384
[7]   Total synthesis of tryprostatin B: Generation of a nucleophilic prenylating species from a prenylstannane [J].
Depew, KM ;
Danishefsky, SJ ;
Rosen, N ;
SeppLorenzino, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (49) :12463-12464
[8]  
Hamaker L. K., 1995, ALKALOIDS CHEM BIOL, V9, P23
[9]  
HAMAKER LK, 1995, THESIS U WISCONSIN M
[10]  
LIU R, 1996, THESIS U WISCONSIN M