1.1: tris-(dibenzylideneacetone)dipalladium(0); di-tert-butyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine; potassium carbonate 2.1: lithium diisopropyl amide / -25 °C 3.1: sodium tetrahydroborate 4.1: triethylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 130 °C 5.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate 6.1: tetrahydrofuran / 3 h / -25 °C / |Inert atmosphere 7.1: borane-THF; sodium hydroxide; dihydrogen peroxide / tetrahydrofuran / 3 h / 0 - 20 °C / |Inert atmosphere 8.1: triethylamine; methanesulfonyl chloride / dichloromethane / 20 °C / |Inert atmosphere 8.2: 0.5 h / 20 °C / |Inert atmosphere 8.3: 3 h / |Inert atmosphere 9.1: thionyl chloride / N,N-dimethyl acetamide / 9 h / 20 °C / |Inert atmosphere 10.1: hydrogen bromide / water / 10 h / |Reflux 11.1: palladium 10 on activated carbon; hydrogen / ethanol / 12 h / 20 °C View Scheme

Stage #1: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '906717', constants.ctx, '0')">lithium diisopropyl amide</a> <br /> <br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4921393', constants.ctx, '0')">ozone</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '610776', constants.ctx, '0')">triphenylphosphine</a> <br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.58 h / -78 &deg;C / |Inert atmosphere<br />1.2: 2.67 h / -78 - 24 &deg;C / |Inert atmosphere<br />2.1: ozone / dichloromethane; methanol / -78 &deg;C / |Inert atmosphere<br />2.2: 0.5 h / 24 &deg;C / |Inert atmosphere<br /> <br /> &nbsp;