Tetrahedron

Combinatorial chemistry of natural products: Solid phase synthesis of D-and L-cycloserine derivatives

MF Gordeev, GW Luehr, HC Hui, EM Gordon, DV Patel

Index: Gordeev, Mikhail F.; Luehr, Gary W.; Hui, Hon C.; Gordon, Eric M.; Patel, Dinesh V. Tetrahedron, 1998 , vol. 54, # 52 p. 15879 - 15890

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Citation Number: 40

Abstract

An efficient methodology for a solid phase synthesis of D-and L-cycloserine derivatives is described. Fmoc-D-cycloserine 4 and its L-enantiomer 5 prepared by a selective amine acylation of bis-silylated parent compounds are immobilized on Sasrin or 2-chlorotrityl linker resins using Mitsunobu-type reaction or direct tritylation, respectively. The resulting Fmoc- cycloserine resins 7, 10, and 11 are deprotected with piperidine in DMF or DCM to ...