Tetrahedron: Asymmetry

Synthesis of natural and non natural orthogonally protected lanthionines from N-tritylserine and allo-threonine derivatives

C Dugave, A Ménez

Index: Dugave, Christophe; Menez, Andre Tetrahedron Asymmetry, 1997 , vol. 8, # 9 p. 1453 - 1465

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Citation Number: 46

Abstract

The reactivity of electrophiles derived from N-tritylserine, threonine and allo-threonine esters toward a selection of nucleophiles was investigated. Best yields from substitution products were obtained with N-trityliodoalanine and soft nucleophiles such as thiols. This strategy was applied to the synthesis of lanthionines, the monosulfide analogs of cystine. Orthogonally protected sulfide adducts from L-and D-cysteines, threo-β-methyl-L-cysteine ...