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Chiral synthesis of tri-O-methylimbricatine, an etherified derivative of the starfish alkaloid imbricatine

TitleChiral synthesis of tri-O-methylimbricatine, an etherified derivative of the starfish alkaloid imbricatine
Publication TypeJournal Article
Year of Publication1998
AuthorsOhba, M, Nishimura, Y, Imasho, M, Fujii, T, Kubanek, J, Andersen, RJ
JournalTetrahedron Letters
Volume39
Pagination5999-6002
Date PublishedAug
Type of ArticleArticle
ISBN Number0040-4039
Keywordsamino acids and derivatives, AMINO-ACIDS, DERMASTERIAS-IMBRICATA, imidazoles/imidazolines, isoquinolines, REAGENTS, thioethers
Abstract

A chiral synthesis of tri-O-methylimbricatine (2), the tri-O-methyl derivative of the unique benzyltetrahydroisoquinoline alkaloid imbricatine (1) isolated from the starfish Dermasterias imbricata, has been accomplished. As a result of the synthesis, the correctness of the structure and absolute stereochemistry proposed for imbricatine has been unequivocally confirmed. (C) 1998 Elsevier Science Ltd. All rights reserved.
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