Multi-step reaction with 13 steps
1: t-BuOOH, SeO2 / CH2Cl2 / 240 h / 25 °C
2: Zn dust, NaOAc, NaI / acetic acid / 25 h
3: CO/H2 / RhH(Co)(PPh3)3 / hexane / 6 h / 110 °C / 150012 Torr
4: LiAlH4 / diethyl ether / 2 h / Heating
5: pyridine / 2 h / Ambient temperature
6: hexamethyldisilazane, pyridine / 48 h / Heating
7: LiAlH4 / diethyl ether / 1 h / Heating
8: PDC, NaOAc / CH2Cl2 / 2 h / Ambient temperature
9: 1.) BuLi / diethyl ether; hexane / 1.) 4 h, RT, 2.) reflux, 5 h
10: 1.) BBN, 2.) 30percent H2O2, 10percent NaOH / 1.) THF, 0 deg C, 5 h, RT, 18h, 2.) H2O, 1 h
11: PDC, NaOAc / CH2Cl2
12: 1.) BuLi / diethyl ether; hexane / 1 h / Heating
13: HCl, H2O / methanol / 1 h
With
pyridine; hydrogenchloride; tert.-butylhydroperoxide; sodium hydroxide; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; selenium(IV) oxide; carbon monoxide; BBN; water; hydrogen; dihydrogen peroxide; sodium acetate; 1,1,1,3,3,3-hexamethyl-disilazane; sodium iodide; zinc;
carbonylhydridetris(triphenylphosphine)rhodium(I);
In
methanol; diethyl ether; hexane; dichloromethane; acetic acid;
DOI:10.1002/hlca.19860690321