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

doi:10.1021/ol048462v

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 journal › Article › peer-review

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 language	English
Pages (from-to)	3909-3912
Number of pages	4
Journal	Organic Letters
Volume	6
DOIs	https://doi.org/10.1021/ol048462v
Publication status	Published - 28 Oct 2004

Keywords

TUBE FORMATION INHIBITORS
STREPTOMYCES SP
ALDOL REACTIONS
ANGIOGENESIS
FAMILY
UCS15A

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10.1021/ol048462v

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

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.",

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author = "Davies, {M W} and L Maskell and M Shipman and Slawin, {A M Z} and Vidot, {S M E} and Whatmore, {J L}",

year = "2004",

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doi = "10.1021/ol048462v",

language = "English",

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journal = "Organic Letters",

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T1 - Studies toward the synthesis of luminacin D: Assembly of simplified analogues devoid of the epoxide displaying antiangiogenic activity

AU - Davies, M W

AU - Maskell, L

AU - Shipman, M

AU - Slawin, A M Z

AU - Vidot, S M E

AU - Whatmore, J L

PY - 2004/10/28

Y1 - 2004/10/28

N2 - [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.

AB - [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.

KW - TUBE FORMATION INHIBITORS

KW - STREPTOMYCES SP

KW - ALDOL REACTIONS

KW - ANGIOGENESIS

KW - FAMILY

KW - UCS15A

UR - http://www.scopus.com/inward/record.url?scp=8744312668&partnerID=8YFLogxK

U2 - 10.1021/ol048462v

DO - 10.1021/ol048462v

M3 - Article

SN - 1523-7060

VL - 6

SP - 3909

EP - 3912

JO - Organic Letters

JF - Organic Letters

ER -

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

Abstract

Keywords

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