Synthesis of a novel polyhydroxylated salicylic acid lactone framework

J. S.Shane Rountree; Paul V. Murphy

doi:10.1021/ol802852r

Synthesis of a novel polyhydroxylated salicylic acid lactone framework

J. S.Shane Rountree
, Paul V. Murphy

Infectious Disease

University College Dublin

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

24 Citations (Scopus)

Abstract

The facile preparation of a novel 8-membered polyhydroxylated salicylic acid lactone from 2,6-dihydroxybenzoic acid and sodium thio-D-glucose is described. The key step involved a sodium hydride promoted intramolecular lactonization in the presence of excess TMSCl, which led to isolation of the "natural product like" lactone.

Original language	English
Pages (from-to)	871-874
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	4
DOIs	https://doi.org/10.1021/ol802852r
Publication status	Published - 19 Feb 2009

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title = "Synthesis of a novel polyhydroxylated salicylic acid lactone framework",

abstract = "The facile preparation of a novel 8-membered polyhydroxylated salicylic acid lactone from 2,6-dihydroxybenzoic acid and sodium thio-D-glucose is described. The key step involved a sodium hydride promoted intramolecular lactonization in the presence of excess TMSCl, which led to isolation of the {"}natural product like{"} lactone.",

author = "Rountree, \{J. S.Shane\} and Murphy, \{Paul V.\}",

year = "2009",

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AU - Rountree, J. S.Shane

AU - Murphy, Paul V.

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N2 - The facile preparation of a novel 8-membered polyhydroxylated salicylic acid lactone from 2,6-dihydroxybenzoic acid and sodium thio-D-glucose is described. The key step involved a sodium hydride promoted intramolecular lactonization in the presence of excess TMSCl, which led to isolation of the "natural product like" lactone.

AB - The facile preparation of a novel 8-membered polyhydroxylated salicylic acid lactone from 2,6-dihydroxybenzoic acid and sodium thio-D-glucose is described. The key step involved a sodium hydride promoted intramolecular lactonization in the presence of excess TMSCl, which led to isolation of the "natural product like" lactone.

UR - https://www.scopus.com/pages/publications/62749123503

U2 - 10.1021/ol802852r

DO - 10.1021/ol802852r

M3 - Article

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VL - 11

SP - 871

EP - 874

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

Synthesis of a novel polyhydroxylated salicylic acid lactone framework

Abstract

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