Multi-step reaction with 13 steps
1.1: 9-BBN / tetrahydrofuran / 6 h / 20 °C
1.2: 60 percent / K3PO4*H2O; PCy3 / Pd(OAc)2 / tetrahydrofuran / 24 h / 20 °C
2.1: 85 percent / DDQ; H2O / CH2Cl2 / 0 - 20 °C
3.1: activated molecular sieves 4 Angstroem; NMO; TPAP / CH2Cl2 / 0.5 h / 20 °C
4.1: butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C
4.2: 0.92 g / tetrahydrofuran; hexane / 1 h / 0 °C
5.1: 95 percent / CSA; MeOH / CH2Cl2 / 2 h / 0 °C
6.1: activated molecular sieves 4 Angstroem; NMO; TPAP / CH2Cl2 / 0.5 h / 20 °C
7.1: ethyldiisopropylamine; dibutylboron triflate / CH2Cl2; diethyl ether / -78 - -50 °C
7.2: CH2Cl2; diethyl ether / 6 h / -78 - -50 °C
7.3: 862 mg / aq. H2O2 / methanol; aq. phosphate buffer / pH 7
8.1: Et2BOMe / tetrahydrofuran; methanol / 0.25 h / -70 °C
8.2: 75 percent / NaBH4 / methanol; tetrahydrofuran / 3 h / -70 °C
9.1: 80 percent / ethyldiisopropylamine / CHCl3 / 12 h / 65 °C
10.1: 91 percent / aq. NaOH / tetrahydrofuran; methanol / 2 h / 60 °C
11.1: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 24 h / 20 °C
12.1: 25 percent / 1-methyl-2-chloropyridinium iodide; triethylamine / acetonitrile / Heating
13.1: second generation Grubbs catalyst / CH2Cl2 / 4 h / 45 °C
13.2: 65 percent / CH2Cl2; dimethylsulfoxide / 16 h
With
methanol; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; diethyl methoxy borane; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; water; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; acetonitrile;
1.2: Fu cross-coupling / 4.2: Wittig reaction / 7.2: Evans aldol reaction;
DOI:10.1021/ol070517g