diphenylselenium bis(trifluoroacetate) in ethylene glycol dimethyl ether Ambient temperature;

1: ortho-bromobenzaldehyde; immobilized on REM resin N-acetyldehydroalanine With N,N-dicyclohexylmethylamine; [(t-Bu)3PH]BF4; tris(dibenzylideneacetone)dipalladium(0) chloroform complex in toluene T=100°C; Heck reaction; 18 h; 2: methanol With sodium methylate in tetrahydrofuran T=20°C; 7 h; Further stages.;

1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane T=0 - 20°C; Cyclization; Wittig-Horner reaction;

cesium fluoride in acetonitrile T=20°C; 18 h; Inert atmosphere;

palladium diacetate; triethylamine; tris-(o-tolyl)phosphine in acetonitrile Heating;

1: SOCl2 / 3 h 2: S / xylene / 48 h / Heating View Scheme

palladium in toluene T=110°C; 15 h; regiospecific reaction;

1: With N-chloro-succinimide in diethyl ether T=0 - 20°C; Chlorination; 1 h; 2: With triethylamine in diethyl ether T=0 - 20°C; Dehydrochlorination; 2 h; Further stages.;

1: α-acetylaminoacrylic acid With triphenylphosphine; hydroxymethyl polystyrene resin; diethylazodicarboxylate in tetrahydrofuran; toluene T=20°C; 24 h; 2: ortho-bromobenzaldehyde With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; N,N-dicyclohexylmethylamine; [(t-Bu)3PH]BF4 in toluene T=100°C; Heck reaction; 18 h; 3: sodium methylate in tetrahydrofuran; methanol T=20°C; 7 h;

1: 2) acid 2: 91 percent / (EtO)3P / benzene / 21 h / Ambient temperature View Scheme