Multi-step reaction with 11 steps
1: naphthalene; lithium / 3 h / -20 °C
2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 6 h / 0 - 20 °C
3: n-butyllithium / anhydride THF / 3 h / -20 °C
4: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 - 20 °C
5: pyridinium p-toluenesulfonate / dichloromethane / 0.5 h / 0 °C
6: sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 4 h / 27 °C
7: (R,R)-bis[iPrO-Ti(1,1'-binaphthyl-2,2'-diyldioxy)]O / dichloromethane / 72 h / -20 °C / Molecular sieve
8: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / -78 °C
9: Grubbs catalyst first generation / dichloromethane / 12 h / Reflux
10: hydrogenchloride / methanol / 0.5 h / 0 °C
11: quinoline; Lindlar's catalyst; hydrogen / methanol; ethyl acetate / 6 h / 20 °C
With
Grubbs catalyst first generation; quinoline; hydrogenchloride; sodium periodate; osmium(VIII) oxide; n-butyllithium; naphthalene; (R,R)-bis[iPrO-Ti(1,1'-binaphthyl-2,2'-diyldioxy)]O; Lindlar's catalyst; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; lithium; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; anhydride THF; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetone;
7: Maruoka asymmetric allylation;
DOI:10.1016/j.bmcl.2012.02.025