Ethanol → (9H-fluoren-9-yl)methyl(E)-3-((S)-7-methoxy-8-(3-((S)-7-methoxy-5,11-dioxo-2-((E)-prop-1-enyl)-10-((2-(trimethylsilyl)ethoxy)methyl)-5,10,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yloxy)propoxy)-5,11-dioxo-10-((2-(trimethylsilyl)ethoxy)methyl)-5,10,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)allylcarbamate

Participants

Reaction Conditions

Reaction Steps

Trans-1-propen-1-ylboronic acid (0.103 g, 1.20 mmol, 3.0 eq.), triethylamine (0.220 ml, 1.60 mmol, 4.0 eq.) and mono triflate 13 (0.500 g, 0.401 mmol, 1.0 eq.) were dissolved in a mixture of ethanol (10 mL), toluene (20 mL) and water (3 mL) under a nitrogen atmosphere. The reaction mixture was degassed under nitrogen for 5 minutes and tetrakis(triphenylphosphine)palladium(0) (0.018 g, 0.016 mmol, 0.04 eq.) added. The reaction mixture was stirred at 60° C. for 50 minutes, then concentrated to dryness under reduced pressure and the crude solid was purified by flash chromatography (silica gel, 50:50 acetate/hexane v/v then 66:33 ethyl acetate/hexane v/v) to afford the product as pale yellow solid. (0.35 g, 77%). LC/MS (3.910 min (ES+)), m/z: 1137.86 [M+H]+.

Provenance & Evidence