Multi-step reaction with 21 steps
1: H2O2, NaOH / methanol / 2 h / 0 °C
2: H2 / PtO2 / ethanol / 12 h / 25 °C
3: 1.) LDA / 2.) THF, from -78 to 0 deg C, 2 h
4: Et3N / CH2Cl2 / 12 h
5: 93 percent / L-selectride / tetrahydrofuran / 2 h / -78 °C
6: Et3N / CH2Cl2 / 0.5 h / 0 °C
7: sodium naphthalenide / tetrahydrofuran / 0.5 h / 0 °C
8: 74 percent / propionic acid / 72 h / 170 °C
9: 97 percent / DIBAL / CH2Cl2 / 0.5 h / -78 °C
10: 1.) NaH / 1.) THF, 25 deg C, 30 min, 2.) THF, from 0 to 25 deg C, 5 h
11: 91 percent / DIBAL / CH2Cl2 / 2 h / -78 °C
12: 91 percent / diethyl L-tartrate, mol. sieves 4A, Ti(OiPr)4, t-BuOOH / CH2Cl2 / 8 h / -20 °C
13: Et3N / CH2Cl2 / 1 h / -20 °C
14: sodium naphthalenide / tetrahydrofuran / 0.17 h / 0 °C
15: pyridinium p-toluenesulfonate / CH2Cl2 / 48 h / 25 °C
16: 1.) Hg(OAc)2, 2.) Li2PdCl4, CuCl2 / 1.) MeOH, 25 deg C, 12 h, 2.) MeOH, 55 deg C, 3 h
17: CH2Cl2; tetrahydrofuran / 6 h / -78 °C
18: TBAF / tetrahydrofuran / 2 h / 25 °C
19: Dess-Martin periodinane, NaHCO3, pyridine / 4 h / 25 °C
20: β-alanine / aq. ethanol / 72 h / 25 °C
21: (iPr)2NEt / CH2Cl2 / 2 h / -78 °C
With
pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; lithium tetrachloropalladate(II); diethyl (2R,3R)-tartrate; 4 A molecular sieve; mercury(II) diacetate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; L-Selectride; sodium naphthalenide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; propionic acid; triethylamine; N-ethyl-N,N-diisopropylamine; copper dichloride; lithium diisopropyl amide; 3-amino propanoic acid;
platinum(IV) oxide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane;
DOI:10.1021/ja981062g