Total Syntheses of Leuconoxine, Leuconodine B, and Melodinine E by Oxidative Cyclic Aminal Formation and Diastereoselective Ring-Closing Metathesis

Total Syntheses of Leuconoxine, Leuconodine B, and Melodinine E by Oxidative Cyclic Aminal Formation and Diastereoselective Ring-Closing Metathesis

Total syntheses of leuconodine B, melodinine E, and leuconoxine were accomplished via a divergent route. The [5.5.6.6]­diaza­fenestrane skeleton was constructed from an indole-3-acetamide derivative via DMDO oxidation to hydroxyl­indole­nine, TMSOTf/2,6-lutidine mediated cyclic aminal formation, and...

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Veröffentlicht in:Organic letters 2014-05, Vol.16 (9), p.2526-2529
Hauptverfasser: Umehara, Atsushi, Ueda, Hirofumi, Tokuyama, Hidetoshi
Format: Artikel
Sprache:eng
Schlagworte:
Cyclization
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Molecular Structure
Oxidation-Reduction
Secologanin Tryptamine Alkaloids - chemical synthesis
Secologanin Tryptamine Alkaloids - chemistry
Stereoisomerism
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Zusammenfassung:Total syntheses of leuconodine B, melodinine E, and leuconoxine were accomplished via a divergent route. The [5.5.6.6]­diaza­fenestrane skeleton was constructed from an indole-3-acetamide derivative via DMDO oxidation to hydroxyl­indole­nine, TMSOTf/2,6-lutidine mediated cyclic aminal formation, and diastereoseletive ring-closing metathesis of a triene derivative.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol500903e