Facile Synthesis of (R,R) and of (R,S) Tricarballylic Acid Anhydride and Imide Derivatives.docVIP

Molecules 2000, 5, 665-673 molecules ISSN 1420-3049 Facile Synthesis of (R,R) and of (R,S) Tricarballylic Acid Anhydride and Imide Derivatives Abdel-Sattar S. Hamad Elgazwy Department of Chemistry, Faculty of Science, University of Ain Shams, Abbassia 11566, Cairo, Egypt Tel.: (00)202-4831836, Fax: (00)202-4831836, E-mail: hamad@asunet.shams.eun.eg Received:17 May 1999;revised form:23 March 2000 /Accepted:3April 2000 /Published:15 April 2000 Abstract: The diastereomeric mixture of (R)-2-(methoxycarbonylmethyl)-N-(R)-1-(1- phenylethyl) succinimide 11s and (S)-2-(methoxycarbonylmethyl)-N-(R)-1-(1-phenylethyl) succinimide 11a was synthesized by reaction of 2-(carboxymethyl)succinic anhydride 6 with (R)-(α)-methylbenzylamine in dry THF/room temperature/24 hrs. The diastereomeric mixture of 1-[(R)-(α)-Methylbenzylamideformyl)]propane-2,3-dicarboxylic acid anhydride 9s and 1-[(R)-(α)-methylbenzylamideformyl)]propane-2,3-dicarboxylic acid anhydride 9a was isolated as an intermediate under the reaction conditions. This diastereomeric mixture 9s/9a was also prepared by a different route via reaction of 1-(chloroformyl)propane-2,3- dicarboxylic acid anydride 12 with (R)-(α)-methylbenzylamine in the presence of DMA at 0oC for 24 hrs. Keywords: Fumonisin, AAL Toxin TA, Actinoplanic acid, Diastereomers of Tricarballylic acid, Sphingosine analogs. Introduction Tricarballylic acid (TCA) 5 is found as a fragment in several mycotoxin natural products such as Fumonisin B1 (1a), Fumonisin B2 (2b), and AAL Toxin TA (3) and a macrocyclic polycarboxylic acid which is an inhibitor of Ras Farnesyl-Protein Transferase (FPTase) [1] like Actinoplanic acid (4), (Figure 1). Fumonisins and AAL toxins are sphingosine analog mycotoxins characterized by tricar- ? 2000 by MDPI (). Reproduction is permitted for noncommercial purposes.  666 Molecules 2000, 5 ballylic acid side chains.[2] Most notably, fumo