A high yielding synthesis of anthranilate esters from sterically hindered alcohols

David Barker; Malcolm D. McLeod; Margaret A. Brimble; G. Paul Savage

doi:10.1016/S0040-4039(00)02327-3

A high yielding synthesis of anthranilate esters from sterically hindered alcohols

David Barker, Malcolm D. McLeod^*, Margaret A. Brimble, G. Paul Savage

^*Corresponding author for this work

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

22 Citations (Scopus)

Abstract

A high yielding and operationally simple synthesis of anthranilate esters derived from primary, secondary and tertiary alcohols is reported. Esterification of the alcohol with N-(trifluoroacetyl)anthranilic acid under Steglich conditions, followed by sodium borohydride mediated cleavage of the trifluoroacetyl group affords the anthranilate ester. This new method has application in the synthesis of the ester sidechains of the commonly occurring Delphinium and Aconitum alkaloids and their analogues.

Original language	English
Pages (from-to)	1785-1788
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	9
DOIs	https://doi.org/10.1016/S0040-4039(00)02327-3
Publication status	Published - 26 Feb 2001
Externally published	Yes

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10.1016/S0040-4039(00)02327-3

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abstract = "A high yielding and operationally simple synthesis of anthranilate esters derived from primary, secondary and tertiary alcohols is reported. Esterification of the alcohol with N-(trifluoroacetyl)anthranilic acid under Steglich conditions, followed by sodium borohydride mediated cleavage of the trifluoroacetyl group affords the anthranilate ester. This new method has application in the synthesis of the ester sidechains of the commonly occurring Delphinium and Aconitum alkaloids and their analogues.",

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T1 - A high yielding synthesis of anthranilate esters from sterically hindered alcohols

AU - Barker, David

AU - McLeod, Malcolm D.

AU - Brimble, Margaret A.

AU - Savage, G. Paul

PY - 2001/2/26

Y1 - 2001/2/26

N2 - A high yielding and operationally simple synthesis of anthranilate esters derived from primary, secondary and tertiary alcohols is reported. Esterification of the alcohol with N-(trifluoroacetyl)anthranilic acid under Steglich conditions, followed by sodium borohydride mediated cleavage of the trifluoroacetyl group affords the anthranilate ester. This new method has application in the synthesis of the ester sidechains of the commonly occurring Delphinium and Aconitum alkaloids and their analogues.

AB - A high yielding and operationally simple synthesis of anthranilate esters derived from primary, secondary and tertiary alcohols is reported. Esterification of the alcohol with N-(trifluoroacetyl)anthranilic acid under Steglich conditions, followed by sodium borohydride mediated cleavage of the trifluoroacetyl group affords the anthranilate ester. This new method has application in the synthesis of the ester sidechains of the commonly occurring Delphinium and Aconitum alkaloids and their analogues.

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U2 - 10.1016/S0040-4039(00)02327-3

DO - 10.1016/S0040-4039(00)02327-3

M3 - Article

SN - 0040-4039

VL - 42

SP - 1785

EP - 1788

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 9

ER -

A high yielding synthesis of anthranilate esters from sterically hindered alcohols

Abstract

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