Multi-step reaction with 12 steps
1.1: n-BuLi / toluene; tetrahydrofuran / 3 h / -30 °C
1.2: 87 percent / tetrahydrofuran; toluene / 0.5 h / -30 °C
2.1: 90 percent / Dess-Martin periodinane; pyridine / CH2Cl2 / 3 h / 0 °C
3.1: 89 percent / TMSOTf / CH2Cl2 / 0.17 h / -90 °C
4.1: DMSO; oxalyl dichloride; Et3N / CH2Cl2 / -78 - 0 °C
5.1: n-BuLi / tetrahydrofuran; hexane / 1.33 h / -78 - 0 °C
5.2: 3.30 g / tetrahydrofuran; hexane / 2.5 h / 0 °C
6.1: 60 percent / Grubb's 2nd generation catalyst / CH2Cl2 / 12 h / 40 °C
7.1: 90 percent / PhI(OTf)2 / acetonitrile; various solvent(s) / 0.67 h / 0 °C / pH 7
8.1: LDA / tetrahydrofuran; hexane / -78 °C
8.2: 81 percent / N-tert-butylbenzenesulfinimidoyl chloride / tetrahydrofuran; hexane / 0.75 h / -78 °C
9.1: 80 percent / NaBH4; CeCl3*7H2O / methanol / 0.67 h / -65 °C
10.1: 87 percent / pyridine; 4-DMAP / CH2Cl2 / 3 h / -10 °C
11.1: 82 percent / Pd2(dba)3*CHCl3; n-Bu3P; LiBH4 / 1,2-dimethoxy-ethane / 1.5 h / 0 °C
12.1: 92 percent / DIBAL-H / CH2Cl2 / 0.33 h / -78 °C
With
pyridine; dmap; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium tetrahydroborate; lithium borohydride; n-butyllithium; cerium(III) chloride; oxalyl dichloride; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; phenyl[(trifluoromethane)sulfonyloxy]-lambda-3-iodanyl trifluoromethanesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; toluene; acetonitrile;
4.1: Swern oxidation;
DOI:10.1021/ja054750q