Multi-step reaction with 13 steps
1.1: neat (no solvent) / Reflux
2.1: triethylamine / dichloromethane / 20 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / -40 °C
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; dmap / dichloromethane-d2 / 0 - 20 °C
5.1: K2OsO2*2H2O; potassium hexacyanoferrate(III); 9-O-(9'-Phenanthryl)-dihydroquinine / 20 h / 0 °C
6.1: camphor-10-sulfonic acid / dichloromethane / Reflux
7.1: diisobutylaluminium hydride / toluene / 100 °C
8.1: Dess-Martin periodane / dichloromethane / 20 °C
9.1: n-butyllithium / tetrahydrofuran / -78 °C
9.2: -78 °C
10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C
11.1: toluene-4-sulfonic acid / methanol / 20 °C
12.1: Dess-Martin periodane / dichloromethane / 20 °C
13.1: methylmagnesium halide / tetrahydrofuran / 0 °C
13.2: 20 °C
With
dmap; lithium aluminium tetrahydride; n-butyllithium; camphor-10-sulfonic acid; K2OsO2*2H2O; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; 9-O-(9'-Phenanthryl)-dihydroquinine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III);
In
tetrahydrofuran; methanol; dichloromethane; dichloromethane-d2; toluene;
1.1: |Diels-Alder Cycloaddition / 5.1: |Sharpless Dihydroxylation / 8.1: |Dess-Martin Oxidation / 12.1: |Dess-Martin Oxidation / 13.2: |Dess-Martin Oxidation;
DOI:10.1016/j.tetlet.2013.01.115