First total synthesis of oteromycin utilizing one-pot four-step cascade reaction strategy

The first total synthesis of oteromycin was investigated. Our previously reported convergent strategy for the synthesis of α-acyl-γ-hydroxy-γ-lactams was first applied for the total synthesis, however, the final deprotection of the methoxyaminal moiety could not be achieved since an unexpected intra...

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Veröffentlicht in:	Tetrahedron letters 2013-02, Vol.54 (6), p.506-511
Hauptverfasser:	Uchiro, Hiromi, Shionozaki, Nobuhiro, Tanaka, Ryo, Kitano, Hiroyuki, Iwamura, Naoki, Makino, Kimiko
Format:	Artikel
Sprache:	eng
Schlagworte:	Cascade chemical reactions Cascade reaction Stereochemistry Strategy Synthesis (chemistry) Tetrahedrons Total synthesis α-Acyl-γ-hydroxylactam
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container_end_page	511
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container_title	Tetrahedron letters
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creator	Uchiro, Hiromi Shionozaki, Nobuhiro Tanaka, Ryo Kitano, Hiroyuki Iwamura, Naoki Makino, Kimiko
description	The first total synthesis of oteromycin was investigated. Our previously reported convergent strategy for the synthesis of α-acyl-γ-hydroxy-γ-lactams was first applied for the total synthesis, however, the final deprotection of the methoxyaminal moiety could not be achieved since an unexpected intramolecular Diels–Alder (IMDA) reaction occurred. Therefore, a novel one-pot four-step cascade reaction starting from α-selenolactam was investigated. The efficient synthetic strategy was successfully developed to afford the desired oteromycin, and its complete structure elucidation including the stereochemistry at C24 position was also accomplished.
doi_str_mv	10.1016/j.tetlet.2012.11.073
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source	ScienceDirect Journals (5 years ago - present)
subjects	Cascade chemical reactions Cascade reaction Stereochemistry Strategy Synthesis (chemistry) Tetrahedrons Total synthesis α-Acyl-γ-hydroxylactam
title	First total synthesis of oteromycin utilizing one-pot four-step cascade reaction strategy
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