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

Authors
Raunkjaer, M Pedersen, DS Elsey, GM Sefton, MA Skouroumounis, GK
Citation
M. Raunkjaer et al., Precursors to oak lactone: synthesis of gallate ester derivatives of 3-methyl-4-hydroxyoctanoic acid, TETRAHEDR L, 42(49), 2001, pp. 8717-8719
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
49
Year of publication
2001
Pages
8717 - 8719
Database
ISI
SICI code
0040-4039(200112)42:49<8717:PTOLSO>2.0.ZU;2-2
Abstract
(3R,4R- and 3S,4S)-3-Methyl-4-(3'-O-methylgalloyloxy)octanoic acid (2b), th e corresponding methyl ester (2c) and the straight galloyl derivative, (3R, 4R- and 3S,4S)-3-methyl-4-galloyloxyoctanoic acid (2a) were synthesised fro m cis-oak lactone (1). Analysis by TLC and mass spectrometry established th at the original assignment of structure (2c) to a methylated natural oak co mponent was in error. (C) 2001 Elsevier Science Ltd. All rights reserved.