TY - JOUR T1 - Expeditious convergent synthesis of a dibromotyrosine alkaloid inhibitor of mycothiol-S-conjugate amidase JF - Tetrahedron Letters Y1 - 2005 A1 - Chanda, B. M. A1 - Sulake, R. S. KW - 4-hydroxybenzaldehyde KW - marine alkaloid KW - mycothiol-S-conjugate amidase AB -

A quick, economic synthesis of the alkaloid 1, an inhibitor of mycothiol-S-conjugate amidase (MCA) is reported. Starting from low-cost, commercially available 4-hydroxybenzaldehyde, the nine-step synthesis involved dibromination and coupling with N-acetylglycine to give a stable methyloxazole intermediate 5 which was hydrolyzed, oximated and coupled to agmatine to yield the oxime in -30% overall yield. It was not necessary to protect the oxime in the synthetic sequence thereby circumventing a deprotection step. (c) 2005 Elsevier Ltd. All rights reserved.

PB - PERGAMON-ELSEVIER SCIENCE LTD CY - THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND VL - 46 IS - 38 U3 - Foreign U4 - 2.347 ER -