Studies toward the synthesis of luminacin D: Assembly of simplified analogues devoid of the epoxide displaying antiangiogenic activity

M W Davies, L Maskell, M Shipman, A M Z Slawin, S M E Vidot, J L Whatmore

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

[GRAPHICS]

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.

Original languageEnglish
Pages (from-to)3909-3912
Number of pages4
JournalOrganic Letters
Volume6
DOIs
Publication statusPublished - 28 Oct 2004

Keywords

  • TUBE FORMATION INHIBITORS
  • STREPTOMYCES SP
  • ALDOL REACTIONS
  • ANGIOGENESIS
  • FAMILY
  • UCS15A

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