Studies Toward the Synthesis of Luminacin D: Assembly of Simplified Analogues Devoid of the Epoxide Displaying Antiangiogenic Activity
A series of structurally simplified luminacin analogues devoid of the epoxide ring are assembled in a stereocontrolled manner from 2,4-dimethoxybenzaldehyde using a syn-selective aldol reaction as the key step. The success of the approach is critically dependent on the nature and extent of the alcoh...
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Veröffentlicht in: | Organic letters 2004-10, Vol.6 (22), p.3909-3912 |
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Hauptverfasser: | , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | A series of structurally simplified luminacin analogues devoid of the epoxide ring are assembled in a stereocontrolled manner from 2,4-dimethoxybenzaldehyde using a syn-selective aldol reaction as the key step. The success of the approach is critically dependent on the nature and extent of the alcohol protecting groups. The synthetic analogues inhibit VEGF-stimulated angiogenesis in an in vitro assay indicating that the epoxide is not essential for biological activity in this compound class. |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/ol048462v |