Methods in synthesis of flavonoids. Part 2: High yield access to both enantiomers of catechin

B. Nay; J. P. Monti; A. Nuhrich; G. Deffieux; J. M. Merillon; J. Vercauteren

doi:10.1016/S0040-4039(00)01649-X

Methods in synthesis of flavonoids. Part 2: High yield access to both enantiomers of catechin

B. Nay, J. P. Monti, A. Nuhrich, G. Deffieux, J. M. Merillon, J. Vercauteren

Univ. Bordeaux

Research output: Contribution to journal › Article › peer-review

Abstract

Resolution of racemic synthetic tetra-O-benzylcatechin 2 is described, through the formation of esters S and 6 derived from dibenzoyl-L-tartaric acid. The diastereoisomer of the natural series 6 was separated by crystallization, the other one being an oil. This process allowed us to prepare enantiomerically pure (+)-catechin 8 in high yield. The pure isomer in the ent-series 9 could be obtained, following the same scheme of reactions. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	9049-9051
Number of pages	3
Journal	Tetrahedron Letters
Volume	41
Issue number	47
DOIs	https://doi.org/10.1016/S0040-4039(00)01649-X
Publication status	Published - 18 Nov 2000
Externally published	Yes

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title = "Methods in synthesis of flavonoids. Part 2: High yield access to both enantiomers of catechin",

abstract = "Resolution of racemic synthetic tetra-O-benzylcatechin 2 is described, through the formation of esters S and 6 derived from dibenzoyl-L-tartaric acid. The diastereoisomer of the natural series 6 was separated by crystallization, the other one being an oil. This process allowed us to prepare enantiomerically pure (+)-catechin 8 in high yield. The pure isomer in the ent-series 9 could be obtained, following the same scheme of reactions. (C) 2000 Elsevier Science Ltd.",

author = "B. Nay and Monti, \{J. P.\} and A. Nuhrich and G. Deffieux and Merillon, \{J. M.\} and J. Vercauteren",

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T2 - High yield access to both enantiomers of catechin

AU - Nay, B.

AU - Monti, J. P.

AU - Nuhrich, A.

AU - Deffieux, G.

AU - Merillon, J. M.

AU - Vercauteren, J.

PY - 2000/11/18

Y1 - 2000/11/18

N2 - Resolution of racemic synthetic tetra-O-benzylcatechin 2 is described, through the formation of esters S and 6 derived from dibenzoyl-L-tartaric acid. The diastereoisomer of the natural series 6 was separated by crystallization, the other one being an oil. This process allowed us to prepare enantiomerically pure (+)-catechin 8 in high yield. The pure isomer in the ent-series 9 could be obtained, following the same scheme of reactions. (C) 2000 Elsevier Science Ltd.

AB - Resolution of racemic synthetic tetra-O-benzylcatechin 2 is described, through the formation of esters S and 6 derived from dibenzoyl-L-tartaric acid. The diastereoisomer of the natural series 6 was separated by crystallization, the other one being an oil. This process allowed us to prepare enantiomerically pure (+)-catechin 8 in high yield. The pure isomer in the ent-series 9 could be obtained, following the same scheme of reactions. (C) 2000 Elsevier Science Ltd.

U2 - 10.1016/S0040-4039(00)01649-X

DO - 10.1016/S0040-4039(00)01649-X

M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 47

ER -

Methods in synthesis of flavonoids. Part 2: High yield access to both enantiomers of catechin

Abstract

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