Multi-step reaction with 17 steps
1: 1.) LDA, 3.) p-TsOH
2: NaBH4, CeCl3*7H2O / methanol / -20 °C
3: m-CPBA, NaHCO3 / CH2Cl2
4: DMAP / CH2Cl2 / -10 °C
5: Dess-Martin periodinane / Ambient temperature
6: 95 percent / SmI2 / tetrahydrofuran; methanol / -78 °C
7: 90 percent / LDA / tetrahydrofuran / -78 °C
8: Et3N / CH2Cl2 / -10 °C
9: DBU / tetrahydrofuran / Ambient temperature
10: NaBH4, CeCl3*7H2O / methanol / -20 °C
11: 2,4,6-trichlorobenzoyl chloride, Et3N / toluene / Ambient temperature
12: HF, pyridine / tetrahydrofuran / Ambient temperature
13: Dess-Martin periodinane / CH2Cl2 / Ambient temperature
14: 2.) Ac2O, DMAP, 3.) OsO4, NMO, 4.) Pb(OAc)4, Et3N, 5.) DBU
15: 79 percent / DDQ / CH2Cl2; H2O
16: 95 percent / aq. HF / acetonitrile / Ambient temperature
17: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, 2.) DMAP / 1.) toluene, RT, 2.) toluene
With
pyridine; lead(IV) acetate; dmap; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; cerium(III) chloride; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; acetic anhydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile;
DOI:10.1021/ja9727631