82185-41-9Relevant articles and documents
The multicomponent approach to N-methyl peptides: Total synthesis of antibacterial (-)-viridic acid and analogues
Neves Filho, Ricardo A. W.,Stark, Sebastian,Westermann, Bernhard,Wessjohann, Ludger A.
supporting information, p. 2085 - 2090 (2013/02/22)
Two syntheses of natural viridic acid, an unusual triply N-methylated peptide with two anthranilate units, are presented. The first one is based on peptide-coupling strategies and affords the optically active natural product in 20% overall yield over six steps. A more economical approach with only four steps leads to the similarly active racemate by utilizing a Ugi four-component reaction (Ugi-4CR) as the key transformation. A small library of viridic acid analogues is readily available to provide first SAR insight. The biological activities of the natural product and its derivatives against the Gram-negative bacterium Aliivibrio fischeri were evaluated.
Lossen-type rearrangement products in the reaction of N-(phthalimidoyloxy)-3-phenylpropionate and -tosylate with benzyl alcohol
Takagi, Shunsuke,Sheikh, Chanmiya,Ogasawara, Asako,Ohira, Masayuki,Abe, Hitoshi,Morita, Hiroyuki
experimental part, p. 1433 - 1438 (2009/12/24)
This paper reports the reaction of N-(phthalimidoyloxy)-3-phenylpropionate (2a) and -tosylate (6) with benzyl alcohol as a nucleophile to afford the products via Lossen-type rearrangement. To study the scope of this reaction mechanism, we also studied the
A high yielding synthesis of anthranilate esters from sterically hindered alcohols
Barker, David,McLeod, Malcolm D.,Brimble, Margaret A.,Savage, G. Paul
, p. 1785 - 1788 (2007/10/03)
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.
