A practical synthesis of fibrinogen receptor antagonist MK-383. Selective functionalization of (S)-tyrosine
JYL Chung, D Zhao, DL Hughes, EJJ Grabowski
Index: Chung; Zhao; Hughes; Grabowski Tetrahedron, 1993 , vol. 49, # 26 p. 5767 - 5776
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Citation Number: 16
Abstract
A practical 4-step synthesis of fibrinogen receptor antagonist MK-383, N-(n-butanesulfonyl)- O-(4-(4-piperidinyl)-butyl)-(S)-tyrosine, is accomplished in 48% overall yield from (S)- tyrosine. Highlights include:(1) the dual use of 4-picoline as a masked form of piperidine, and as a nucleophile precursor for a 3-carbon homologation with 3-bromo-1- chloropropane;(2) the use of trimethylsilyl groups for temporary protection of phenolic and ...
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[Tetrahedron, , vol. 49, # 26 p. 5767 - 5776]