1.1: triethylamine; hydrogen / platinum on carbon / methanol / 24.25 h / 20 °C 2.1: potassium tert-butylate / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 2.2: -15 - -10 °C / Inert atmosphere View Scheme

hydrogen; triethylamine; platinum on carbon in methanol T=20°C; 24.25 h;

1.1: triethylamine; hydrogen / platinum on carbon / methanol / 24.25 h / 20 °C 2.1: potassium tert-butylate / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 2.2: -15 - -10 °C / Inert atmosphere 3.1: caesium carbonate / N,N-dimethyl-formamide / 3 h / 40 °C View Scheme

1: (5-(ethylamino)-5-oxopentyl)triphenylphosphonium bromide With potassium tert-butylate in tetrahydrofuran T=0°C; 1 h; 2: (3aR,4R,5R,6aS)-4-((S,E)-3-hydroxy-5-phenylpent- 1-enyl)hexahydro-2H-cyclopenta[b]furan-2,5-diol in tetrahydrofuran T=-17°C; Wittig Reaction; 20.5 h;

1: (3aR,4R,5R,6aS)-4-((S,E)-3-hydroxy-5-phenylpent- 1-enyl)hexahydro-2H-cyclopenta[b]furan-2,5-diol; (4-carboxy-n-butyl)-triphenylphosphonium bromide With potassium tert-butylate in tetrahydrofuran T=-12 - 10°C; 2: With sodium carbonate; methyl iodide in N,N-dimethyl-formamide T=25 - 30°C; 12 h; 3: ethylamine in water T=25 - 30°C; 48 h;

sodium hexamethyldisilazane

1.1: potassium tert-butylate / tetrahydrofuran / -15 - -10 °C 2.1: triethylamine; DMEG / tetrahydrofuran / 0.17 h / 30 °C 2.2: 2 h / 30 - 70 °C View Scheme

sodium hexamethyldisilazane

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3570522', constants.ctx, '0')">tetrabutyl ammonium fluoride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a> <br />T=0&deg;C;&nbsp;4&nbsp;h;&nbsp;<br /> <br /> &nbsp;

Stage #1: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4123663', constants.ctx, '0')">diisobutylaluminium hydride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=-80 - -76&deg;C;&nbsp;6&nbsp;h;&nbsp;<br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098229', constants.ctx, '0')">methanol</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=-80 - -76&deg;C;&nbsp;<br /> <br /> &nbsp;