A high yielding synthesis of anthranilate esters from sterically hindered alcohols

Authors
Barker, D McLeod, MD Brimble, MA Savage, GP
Citation
D. Barker et al., A high yielding synthesis of anthranilate esters from sterically hindered alcohols, TETRAHEDR L, 42(9), 2001, pp. 1785-1788
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
9
Year of publication
2001
Pages
1785 - 1788
Database
ISI
SICI code
0040-4039(20010226)42:9<1785:AHYSOA>2.0.ZU;2-K
Abstract
A high yielding and operationally simple synthesis of anthranilate esters d erived from primary, secondary and tertiary alcohols is reported. Esterific ation of the alcohol with N-(trifluoroacetyl)anthranilic acid under Steglic h conditions, followed by sodium borohydride mediated cleavage of the trifl uoroacetyl group affords the anthranilate ester. This new method has applic ation in the synthesis of the eater sidechains of the commonly occurring De lphinium and Aconitum alkaloids and their analogues. (C) 2001 Elsevier Scie nce Ltd. All rights reserved.