Total Synthesis and Structural Revision of (±)-Mauritamide B

被引：0

作者：

Hirozumi, Ryosuke ^{[1
]}

Kudo, Yuta ^{[1
,2
]}

Cho, Yuko ^{[1
]}

Konoki, Keiichi ^{[1
]}

Yotsu-Yamashita, Mari ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Agr Sci, Sendai, Miyagi 9808572, Japan

[2] Tohoku Univ, Frontier Res Inst Interdisciplinary Sci, Sendai, Miyagi 9808578, Japan

来源：

JOURNAL OF NATURAL PRODUCTS | 2025年

基金：

日本学术振兴会;

关键词：

DIMERIC BROMOPYRROLE ALKALOIDS; AGELAS; OROIDIN; CLATHRODIN; IDENTIFICATION; DISPACAMIDES; INHIBITION; SAXITOXIN; IMIDAZOLE;

D O I：

10.1021/acs.jnatprod.5c00019

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Mauritamide B (1a) is a taurine-connected cyclic guanidino-bromopyrrole alkaloid originally isolated from the marine sponge Agelas linnaei. To date, the total synthesis of taurine-connected guanidino-bromopyrrole alkaloids, including this compound, has not yet been reported. Herein, a total synthesis of (+/-)-mauritamide B (1b) was achieved by oxidation of 2-aminoimidazole of dihydro-sventrin (10) using activated carbon and air in the presence of taurine. The synthetic precursor of 10, 4-(3-aminopropyl)-2-aminoimidazole (22), was synthesized via our original route. The NMR data of the obtained product agreed with that reported for mauritamide B (1a). However, a detailed analysis of the NMR data of synthetic (+/-)-mauritamide B (1b) including 1H-15N HSQC spectrum revealed the need for a structural revision of the reported structure for mauritamide B (1b).

引用

页码：806 / 814

页数：9