Total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives

K. Saki Raheem; Nigel P. Botting; Gary Williamson; Denis Barron

doi:10.1016/j.tetlet.2011.10.127

Total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives

K. Saki Raheem, Nigel P. Botting, Gary Williamson, Denis Barron

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

9 Citations (Scopus)

Abstract

We report the first total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives, 3,5-O-diferuloylquinic acid and 3,5-(3,4-dimethoxycinnamyl)quinic acid, in a nine-step sequence. The key step involves Knoevenagel condensations between vanillin, 3,4-dimethoxybenzaldehyde or 4-hydroxy-3-methoxybenzaldehyde and the dimalonate ester of quinic acid.

Original language	English
Pages (from-to)	7175-7177
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	52
DOIs	https://doi.org/10.1016/j.tetlet.2011.10.127
Publication status	Published - 28 Dec 2011
Externally published	Yes

Keywords

Dicaffeoylquinic acids
Knoevenagel condensation
Metabolism references
Natural product synthesis
Plant natural products

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10.1016/j.tetlet.2011.10.127

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title = "Total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives",

abstract = "We report the first total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives, 3,5-O-diferuloylquinic acid and 3,5-(3,4-dimethoxycinnamyl)quinic acid, in a nine-step sequence. The key step involves Knoevenagel condensations between vanillin, 3,4-dimethoxybenzaldehyde or 4-hydroxy-3-methoxybenzaldehyde and the dimalonate ester of quinic acid.",

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author = "Raheem, {K. Saki} and Botting, {Nigel P.} and Gary Williamson and Denis Barron",

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T1 - Total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives

AU - Raheem, K. Saki

AU - Botting, Nigel P.

AU - Williamson, Gary

AU - Barron, Denis

PY - 2011/12/28

Y1 - 2011/12/28

N2 - We report the first total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives, 3,5-O-diferuloylquinic acid and 3,5-(3,4-dimethoxycinnamyl)quinic acid, in a nine-step sequence. The key step involves Knoevenagel condensations between vanillin, 3,4-dimethoxybenzaldehyde or 4-hydroxy-3-methoxybenzaldehyde and the dimalonate ester of quinic acid.

AB - We report the first total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives, 3,5-O-diferuloylquinic acid and 3,5-(3,4-dimethoxycinnamyl)quinic acid, in a nine-step sequence. The key step involves Knoevenagel condensations between vanillin, 3,4-dimethoxybenzaldehyde or 4-hydroxy-3-methoxybenzaldehyde and the dimalonate ester of quinic acid.

KW - Dicaffeoylquinic acids

KW - Knoevenagel condensation

KW - Metabolism references

KW - Natural product synthesis

KW - Plant natural products

UR - http://www.scopus.com/inward/record.url?scp=82255192082&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2011.10.127

DO - 10.1016/j.tetlet.2011.10.127

M3 - Article

AN - SCOPUS:82255192082

VL - 52

SP - 7175

EP - 7177

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 52

ER -

Total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives

Abstract

Keywords

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