Multi-step reaction with 10 steps
1.1: 93 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C
2.1: Ph3P; phenol / benzene / 12 h / 50 °C
2.2: 95 percent / MeI / diethyl ether / 12 h / Heating
3.1: K3Fe(CN)6; K2CO3; MeSO2NH2 / (DHQD)2-PHAL; OsO4 / 2-methyl-propan-2-ol; H2O / 0 °C
3.2: MeI / diethyl ether / 12 h / Heating
3.3: 27.9 g / pyridine; DMAP / CH2Cl2 / -78 - 0 °C
4.1: 90 percent / PPh3; triethylamine; HCOOH / Pd2(dba)3*CHCl3 / tetrahydrofuran / 20 °C
5.1: 59 percent / t-BuOK / tetrahydrofuran / 0 °C
6.1: 89 percent / isopropylmagnesium chloride / tetrahydrofuran; diethyl ether / 0.5 h / cooling
7.1: 86 percent / tetrahydrofuran / 0.5 h / 0 °C
8.1: 76 percent / L-Selectride / tetrahydrofuran / 3 h / -100 °C
9.1: 97 percent / KH; tetrabutylammonium iodide / diethyl ether; tetrahydrofuran / 3 h / 0 °C
10.1: 86 percent / second-generation Grubbs' catalyst / CH2Cl2 / 24 h / Heating
With
n-butyllithium; formic acid; methanesulfonamide; potassium tert-butylate; isopropylmagnesium chloride; tetra-(n-butyl)ammonium iodide; potassium hydride; L-Selectride; potassium carbonate; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); phenol;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; osmium(VIII) oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol; benzene;
2.1: Trost isomerization / 3.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ol062595u