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Asymmetric Total Synthesis of Indole Alkaloids Containing an Indoline Spiroaminal Framework
Author(s) -
Yamada Takeshi,
IdeguchiMatsushita Tetsuya,
Hirose Tomoyasu,
Shirahata Tatsuya,
Hokari Rei,
Ishiyama Aki,
Iwatsuki Masato,
Sugawara Akihiro,
Kobayashi Yoshinori,
Otoguro Kazuhiko,
Ōmura Satoshi,
Sunazuka Toshiaki
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201501150
Subject(s) - indoline , indole test , moiety , total synthesis , chemistry , stereochemistry , imidazole , prenylation , isatin , combinatorial chemistry , organic chemistry , enzyme
The total synthesis of the indole alkaloids, neoxaline, oxaline and meleagrin A, all containing a unique indoline spiroaminal framework, was accomplished through the stereoselective introduction of a reverse prenyl group to the congested benzylic carbon of furoindoline, a two‐pot transformation of indoline (containing three nitrogen atoms at appropriate positions) to the featured indoline spiroaminal framework, and elimination of carbonate assisted by the adjacent imidazole moiety to construct the ( E )‐dehydrohistidine. The absolute stereochemistry of neoxaline was elucidated through our total synthesis. In addition, we evaluated the bioactivity, especially the anti‐infectious properties, of neoxaline and oxaline, and of some synthetic intermediates.