A Facile Synthesis of (+)-L-Discadenine and its Deuterio Derivatives

Jong-Keun Son; Kondareddiar Ramalingam; Ronald W. Woodard

doi:10.1055/s-1988-27529

Synthesis 1988; 1988(3): 240-242
DOI: 10.1055/s-1988-27529

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A Facile Synthesis of (+)-L-Discadenine and its Deuterio Derivatives

Jong-Keun Son^* , Kondareddiar Ramalingam, Ronald W. Woodard

^*Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Michigan, Ann Arbor, MI 48109-1065, USA

Abstract

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The synthesis of discadenine, 3-[(3S)-3-amino-3-carboxypropyl] -6-(3-methyl-2-butenyl)-3H-purine, and several of its deuteriated derivatives, which are useful in the study of the stereochemical mechanism of its biosynthesis, have been synthesized in three steps from the appropriate homoserine lactones via a route designed for maximal synthetic versatility. The yields of discadenine obtained from this new route represent a ten-fold increase over previous procedures.

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