Multi-step reaction with 17 steps
1: Li / tetrahydrofuran / Heating
2: PPTS / CH2Cl2 / 0 - 20 °C
3: n-BuLi / tetrahydrofuran / -78 °C
4: PPTS / methanol / 0 - 20 °C
5: 2-iodoxybenzoic acid / CH2Cl2; dimethylsulfoxide / 20 °C
6: n-BuLi / -78 °C
7: Dess-Martin periodinane; NaHCO3 / 0 - 20 °C
8: 96 percent / i-Pr2NEt; LiCl / acetonitrile / 20 °C
9: 92 percent / AD-mix α; MeSO2NH2; NaHCO3 / 2-methyl-propan-2-ol; H2O / 0 °C
10: 95 percent / PPTS / CH2Cl2 / 0 - 20 °C
11: K-selectride / tetrahydrofuran / -78 °C
12: NaHMDS / tetrahydrofuran; dimethylformamide / 0 °C
13: TBAF / tetrahydrofuran / 0 - 20 °C
14: Et3N / CH2Cl2 / 0 °C
15: NaN3 / dimethylformamide / 90 °C
16: CSA / methanol / 0 - 20 °C
17: 2,6-lutidine / 0 °C
With
2,6-dimethylpyridine; AD-mix-α; n-butyllithium; sodium azide; methanesulfonamide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; lithium; sodium hydrogencarbonate; potassium tri-sec-butyl-borohydride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
9: Sharpless asymmetric dihydroxylation;
DOI:10.1055/s-2007-985585