Total synthesis of graphislactone G

被引:21
作者
Cudaj, Judith [1 ]
Podlech, Joachim [1 ]
机构
[1] KIT, Inst Organ Chem, D-76131 Karlsruhe, Germany
关键词
Polyketides; Fungal metabolites; Resorcylic lactones; Cross Coupling; Suzuki reaction; ENDOPHYTIC FUNGUS; METABOLITES; BIOSYNTHESIS; DERIVATIVES; MYCOBIONTS;
D O I
10.1016/j.tetlet.2010.04.024
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We present a total synthesis of the fungal natural product graphislactone G, a chlorinated resorcylic lactone. The key step is a Suzuki coupling used for the construction of the central biaryl bond. Graphislactone G was prepared in 13 steps with 22% yield starting with orcinol and phloroglucinic acid, where the longest linear sequence consists of nine steps. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3092 / 3094
页数:3
相关论文
共 32 条
[21]  
Nicolaou KC, 2000, CHEM-EUR J, V6, P3095, DOI 10.1002/1521-3765(20000901)6:17<3095::AID-CHEM3095>3.0.CO
[22]  
2-4
[23]  
OVEREEM JC, 1968, RECL TRAV CHIM PAY-B, V87, P940
[24]   SYNTHESIS OF ERIODERMIN [J].
PULGARIN, C ;
GUNZINGER, J ;
TABACCHI, R .
HELVETICA CHIMICA ACTA, 1985, 68 (04) :945-948
[25]   Characterization of graphislactone a as the antioxidant and free radical-scavenging substance from the culture of Cephalosporium sp 1FB-E001, an endophytic fungus in Trachelospermum jasminoides [J].
Song, YC ;
Huang, WY ;
Sun, C ;
Wang, FW ;
Tan, RX .
BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2005, 28 (03) :506-509
[26]   MYCOTOXINS - THEIR BIOSYNTHESIS IN ALTERNARIA [J].
STINSON, EE .
JOURNAL OF FOOD PROTECTION, 1985, 48 (01) :80-91
[27]   Organoborane coupling reactions (Suzuki coupling) [J].
Suzuki, A .
PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES, 2004, 80 (08) :359-371
[28]   6H-Dibenzo[b,d]pyran-6-one derivatives from the cultured lichen mycobionts of Graphis spp. and their biosynthetic origin [J].
Tanahashi, T ;
Takenaka, Y ;
Nagakura, N ;
Hamada, N .
PHYTOCHEMISTRY, 2003, 62 (01) :71-75
[29]  
Tanahashi T, 1997, CHEM PHARM BULL, V45, P1183