Precursors to oak lactone: Synthesis of gallate ester derivatives of 3-methyl-4-hydroxyoctanoic acid

Raunkjar, M.
Pedersen, D.
Elsey, G.
Sefton, M.
Skouroumounis, G.

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Publication date

January 2001

DOI

10.1016/S0040-4039(01)01890-1

Publisher

Elsevier BV

ISSN

0040-4039

Journal

Tetrahedron Letters

Abstract

Copyright © 2001 Elsevier Science Ltd All rights reserved.(3R,4R- and 3S,4S)-3-Methyl-4-(3′-O-methylgalloyloxy)octanoic acid (2b), the corresponding methyl ester (2c) and the straight galloyl derivative, (3R,4R- and 3S,4S)-3-methyl-4-galloyloxyoctanoic acid (2a) were synthesised from cis-oak lactone (1). Analysis by TLC and mass spectrometry established that the original assignment of structure (2c) to a methylated natural oak component was in error. The gallate esters 2a and 2b have been synthesised. A previous assignment of structure 2b to an oak-derived substance is shown to be in error.Michael Raunkjær, D.Sejer Pedersen, Gordon M. Elsey, Mark A. Sefton, and George K. Skouroumounishttp://www.elsevier.com/wps/find/journaldescription.cws_h...

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Precursors to oak lactone: Synthesis of gallate ester derivatives of 3-methyl-4-hydroxyoctanoic acid

Abstract

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Precursors to oak lactone: Synthesis of gallate ester derivatives of 3-methyl-4-hydroxyoctanoic acid

Abstract

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