Synthesis and stereochemistry of 3-hydroxy-5-methylproline, a new naturally occurring imino acid

AB Mauger, OA Stuart, E Katz…

Index: Mauger,A.B.; Stuart,O.A. Journal of Organic Chemistry, 1977 , vol. 42, p. 1000 - 1005

Full Text: HTML

Citation Number: 13

Abstract

The synthetic route (Figure 2) parallels that reported for a synthesis of 3-hydroxyproline,:' except that in the initial step the imino diester 5 was prepared by addition of methyl glycinate to methyl crotonate. Dieckmann cyclization of 6 gave a mixture of isomeric@-keto esters (7 and 8) and reduction of the latter provided a derivative (9) of 3-hydroxy-5-methylproline. Hydrolysis of 9 afforded 3-hydroxy-5-methylproline as an isomeric mixture (10) which was ...