1359015-32-9

Upstream product

• 858669-61-1 (2S,3S)-N-benzyloxycarbonyl-3-methylcysteine methyl ester 
• 634182-11-9 (R)-β-bromo-N-(fluoren-9-ylmethoxycarbonyl)alanine tert-butyl ester 

Downstream Products

• 1359014-81-5 1-O-methyl-3-methyl-7-S-phenyl-(2S,3S,6S)-N₂-(benzyloxycarbonyl)-N₆-(9H-fluoren-9-yl) lanthionate 
• 1359014-82-6 (5S,6S,Z)-methyl 13-(9H-fluoren-9-yl)-6-methyl-3,11-dioxo-1-phenyl-2,12-dioxa-7-thia-4,10-diazatridec-8-ene-5-carboxylate 
• 1359740-84-3 (2S,3S)-methyl 2-(((benzyloxy)carbonyl)amino)-3-(((Z)-2-(((benzyloxy)carbonyl)amino)vinyl)thio)butanoate 
• 1359740-85-4 (2S,3S)-methyl 2-(((benzyloxy)carbonyl)amino)-3-(((E)-2-(((benzyloxy)carbonyl)amino)vinyl)thio)butanoate 
• 1359740-82-1 (2S,3S)-methyl 2-(((benzyloxy)carbonyl)amino)-3-(((R)-2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)-3-oxopropyl)thio)butanoate 
• 1359740-83-2 (R)-2-(((benzyloxy)carbonyl)amino)-3-(((2S,3S)-3-(((benzyloxy)carbonyl)amino)-4-methoxy-4-oxobutan-2-yl)thio)propanoic acid 

Relevant academic research and scientific papers

Decarbonylative approach to the synthesis of enamides from amino acids: Stereoselective synthesis of the (Z)-aminovinyl-d-cysteine unit of mersacidin

The Pd- and Ni-promoted decarbonylation of amino acid thioesters proceeds smoothly to yield enamides. The synthesis of the (S)-(Z)-AviMeCys subunit of mersacidin, an MRSA-active lantibiotic, via this approach, is described.

Synthesis of the AviMeCys-containing D-ring of mersacidin

A chemical synthesis of the D-ring of mersacidin is reported. The synthetic route relied upon development of a method for late-stage introduction of an unusual S-[(Z)-2-aminovinyl]-(3S)-3-methyl-d-cysteine (AviMeCys) functional group via an oxidative decarbonylation/decarboxylation reaction.