Synthesis of Tetrahydropyrroloiminoquinone Alkaloids Based on Electrochemically Generated Hypervalent Iodine Oxidative Cyclization

被引：64
|
作者：
Inoue, Keisuke [1 ]
Ishikawa, Yuichi [1 ]
Nishiyama, Shigeru [1 ]
机构：
[1] Keio Univ, Fac Sci & Technol, Dept Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 03期
关键词：
MARINE NATURAL-PRODUCTS; SPONGE STRONGYLODESMA-ALIWALIENSIS; SULFUR-CONTAINING ALKALOIDS; DISCORHABDIN-C; TOPOISOMERASE-II; ISOBATZELLINE-C; MAKALUVAMINE-A; BATZELLINE-C; DAMIRONE-B; PYRROLOIMINOQUINONE ALKALOIDS;
D O I：
10.1021/ol902566p
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An approach to the synthesis of the tetrahydropyrrololminoquinone alkaloids has been developed and applied to the preparation of N-1-beta-D-ribofuranosyltetrahydropyrroloiminoquinones. The strategy utilizes oxidative cyclization of aryl-methoxyamides by hypervalent iodine to construct the quinoline framework shared by members of this alkaloid family. The hypervalent iodine oxidant is generated in situ by anodic oxidation of iodobenzene.
引用
收藏
页码：436 / 439
页数：4
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