Synthesis of γ, δ-Unsaturated and δ, ε-Unsaturated α-Amino Acids from Fragmentation of γ-and δ-Lactones

JE Tarver, MM Joullié

Index: Tarver Jr., James E.; Joullie, Madeleine M. Journal of Organic Chemistry, 2004 , vol. 69, # 3 p. 815 - 820

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Citation Number: 22

Abstract

A noncoded amino acid of cyclomarin A (1) was synthesized in a racemic fashion. The method employs a six-membered ring template to control the relative stereochemistry and introduction of the functional groups. Ultimately, Pd-catalyzed fragmentation of the lactone provided γ, δ-unsaturated and δ, ε-unsaturated α-amino acids. A Pd-catalyzed ring opening of a γ-lactone is also reported.