Total Synthesis of Dragmacidins G and H

被引：1

作者：

Yamazaki, Keita ^{[1
]}

Okuda, Yuma ^{[1
]}

Takaya, Akiko ^{[1
]}

Nemoto, Tetsuhiro ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Chiba 2608675, Japan

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 03期

关键词：

ASYMMETRIC TOTAL-SYNTHESIS; 1ST TOTAL-SYNTHESIS; SPONGE; (+/-)-DRAGMACIDIN; ELUCIDATION;

D O I：

10.1021/acs.orglett.3c04039

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of dragmacidins G and H was achieved for the first time by employing nucleophilic aromatic substitution and site-selective cross-coupling reactions using appropriately functionalized pyrazines as substrates. The evaluation of antibacterial activities of dragmacidin G, dragmacidin H, and synthetic analogues against Staphylococcus aureus and the efflux pump-deficient Salmonella Typhimurium revealed that the presence of a Br group on the indole ring adjacent to the sulfide unit was important for increasing antibacterial activities.

引用

页码：670 / 675

页数：6

共 50 条

[1] Total Synthesis of Cyanthiwigins A, C, G, and H
Wang, Cheng
Wang, Dan
Gao, Shuanhu
ORGANIC LETTERS, 2013, 15 (17) : 4402 - 4405
[2] Concise total synthesis of naamine G and naamidine H
Koswatta, Panduka B.
Lovely, Carl J.
CHEMICAL COMMUNICATIONS, 2010, 46 (12) : 2148 - 2150
[3] A Convergent and Stereoselective Total Synthesis of Phomolides G and H
Reddy, B. V. Subba
Reddy, P. Sivaramakrishna
Reddy, B. Phaneendra
Yadav, J. S.
SYNLETT, 2014, 25 (04) : 501 - 504
[4] Enantioselective total synthesis of eudistomidins G, H, and I
Ishiyama, Haruaki
Yoshizawa, Kazuaki
Kobayashi, Jun'ichi
TETRAHEDRON, 2012, 68 (31) : 6186 - 6192
[5] First Stereoselective Total Synthesis of Gallicynoic Acids G and H
Krishna, Palakodety Radha
Anitha, Kadimi
HELVETICA CHIMICA ACTA, 2011, 94 (07) : 1246 - 1253
[6] Total Synthesis of Pestalotioprolide G and Putative Structure of Pestalotioprolide H
Paul, Debobrata
Das, Sayantan
Goswami, Rajib Kumar
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (14): : 7437 - 7445
[7] Dragmacidins G and H, Bisindole Alkaloids Tethered by a Guanidino Ethylthiopyrazine Moiety, from a Lipastrotethya sp Marine Sponge
Hitora, Yuki
Takada, Kentaro
Ise, Yuji
Okada, Shigeru
Matsunaga, Shigeki
JOURNAL OF NATURAL PRODUCTS, 2016, 79 (11): : 2973 - 2976
[8] Total Syntheses of Isodomoic Acids G and H: An Exercise in Tetrasubstituted Alkene Synthesis
Ni, Yike
Kassab, Refaie M.
Chevliakov, Maxim V.
Montgomery, John
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (48) : 17714 - 17718
[9] The total synthesis of cannabisin G
Xia, Yamu
Guo, Yinglan
Wen, Yanling
JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2010, 75 (12) : 1617 - 1623
[10] First stereoselective total synthesis of Phomolide G and H via RCM protocol
Ramesh, Palakuri
Reddy, B. Chennakesava
Meshram, H. M.
TETRAHEDRON LETTERS, 2012, 53 (29) : 3735 - 3738

← 1 2 3 4 5 →