Multi-step reaction with 13 steps
1.1: zinc; aq. acetic acid / tetrahydrofuran / 0.08 h / 0 °C
2.1: 592 mg / sodium hypochlorite / H2O; CH2Cl2 / 5 h / 20 °C
3.1: 85 percent / boric acid; H2 / W-2 Raney nickel / H2O; methanol / 6 h / 20 °C
4.1: 89 percent / L-selectride / tetrahydrofuran / 1 h / cooling
5.1: 98 percent / camphorsulfonic acid / 1 h / 20 °C
6.1: 96 percent / H2 / Pd/C / methanol / 20 °C
7.1: 99 percent / imidazole / CH2Cl2 / 20 °C
8.1: 40 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 20 °C
9.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
10.1: lithium hexamethyldisilazide / tetrahydrofuran / 0.5 h / 0 °C
10.2: 96 mg / tetrahydrofuran / 20 °C
11.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C
12.1: 81 percent / 2nd generation Grubbs' catalyst / CH2Cl2 / 22 h / 45 °C
13.1: 88 percent / benzoyl peroxide / acetonitrile / 1 h / 0 - 20 °C
With
1H-imidazole; sodium hypochlorite; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; boric acid; L-Selectride; Dess-Martin periodane; acetic acid; lithium hexamethyldisilazane; zinc; dibenzoyl peroxide;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; W-2 Raney nickel;
In
tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;
9.1: Dess-Martin oxidation / 10.2: Wittig reaction;
DOI:10.1021/ol0701013