Multi-step reaction with 18 steps
1.1: DIBAL-H / CH2Cl2 / 5.5 h / -78 °C
2.1: LiHMDS / tetrahydrofuran / 0.33 h / -78 °C
2.2: 87 percent / tetrahydrofuran / -78 - 20 °C
3.1: SmI2 / tetrahydrofuran / 0.33 h / 0 °C
4.1: 114 mg / H2O; B(OH)3 / tetrahydrofuran / 0.5 h / 20 °C
5.1: 91 percent / Et3B; NaBH4 / methanol; tetrahydrofuran / 17 h / -78 °C
6.1: SOCl2; Et3N / CH2Cl2 / 0.33 h / 0 °C
7.1: 58 mg / Bu4NF*3H2O / tetrahydrofuran / 6 h / Heating
8.1: 79 percent / Et3N; DMAP / CH2Cl2 / 15 h / 20 °C
9.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C
10.1: 4.4 mg / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C
11.1: 86 percent / LDA / tetrahydrofuran / 1 h / -78 °C
12.1: 91 percent / pyridine / CH2Cl2 / 2 h / 0 °C
13.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C
14.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0.13 h / 0 °C
15.1: HF*pyridine / pyridine; tetrahydrofuran / 0 - 20 °C
16.1: 63.2 mg / NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; aq. phosphate buffer / 1.5 h / 0 °C
17.1: 2,4,6-trichlorobenzoyl chloride; Et3N
17.2: 74 percent / 4-dimethylaminopyridine
18.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C
With
pyridine; lead(IV) acetate; dmap; sodium chlorite; sodium tetrahydroborate; osmium(VIII) oxide; thionyl chloride; N-methyl-2-indolinone; samarium diiodide; 2-methyl-but-2-ene; triethyl borane; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; water; boric acid; diisobutylaluminium hydride; ammonium chloride; pyridine hydrogenfluoride; triethylamine; lithium hexamethyldisilazane; zinc; lithium diisopropyl amide;
In
tetrahydrofuran; pyridine; methanol; phosphate buffer; dichloromethane; water; ethyl acetate; tert-butyl alcohol;
16.1: Lindgrin oxidation;
DOI:10.1021/jo015791h