Multi-step reaction with 29 steps
2: 92 percent / imidazole / CH2Cl2
3: 97 percent / BuLi, DMPU / tetrahydrofuran / 1.) -20 deg C; -78 deg C, 2.) -20 deg C
4: 87 percent / imidazole / CH2Cl2
5: 59 percent / tert-BuONa, BuLi / pentane / 1.) -78 deg C, 2.) -78 to -20 deg C
6: 80 percent / PPTS, MeOH
7: 93 percent / NaH, p-toluenesulfonyl imidazole / tetrahydrofuran / 1.) 0 deg C, 2.) 0 deg C
8: 1.) tert-BuLi, 2.) lithium 2-thienylcyanocuprate / 1.) THF, -78 deg C, 2.) -78 to 0 deg C
9: TBAF / 0 °C
10: CaCO3, N-iodosuccinimide / acetonitrile / 0 °C
11: PPTS / acetonitrile
12: Li, NH3 / tetrahydrofuran / -78 °C
13: 93 percent / pyridine / CH2Cl2
14: 87 percent / PPTS, MeOH / 50 °C
15: 94 percent / Et3N, DMAP / CH2Cl2
16: 96 percent / pyridine, DMAP
17: 95 percent / hydrogen fluoride pyridine complex / acetonitrile
18: 91 percent / Dess-Martin periodinane / CH2Cl2
19: 86 percent / NiCl2, CrCl2, (-)-bispyridinyl ligand / tetrahydrofuran
20: 83 percent / Dess-Martin periodinane, pyridine / CH2Cl2
21: H2O, PPTS / acetone
22: Triton-B / methanol; methyl acetate / 0 °C
23: hydrogene fluoride pyridine complex / acetonitrile
24: 79 percent / 2,6-lutidine / -78 °C
25: 82 percent / hydrogene fluoride pyridine complex, pyridine / tetrahydrofuran
26: N-methylmorpholine N-oxide, tetrapropylammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2
27: NaClO2, NaH2PO4, 2-methyl-2-butene / 2-methyl-propan-2-ol
28: 82 percent / Et3N / CH2Cl2
29: 53 percent / DDQ, H2O / CH2Cl2
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; methanol; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium chlorite; sodium dihydrogenphosphate; N-iodo-succinimide; n-butyllithium; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; (-)-bispyridinyl ligand; 4 A molecular sieve; tetrabutyl ammonium fluoride; ammonia; water; tert.-butyl lithium; pyridinium p-toluenesulfonate; N-benzyl-trimethylammonium hydroxide; lithium; sodium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; thien-2-yl(cyano)copper lithium; triethylamine; N-tosylimidazole; 2,3-dicyano-5,6-dichloro-p-benzoquinone; calcium carbonate; nickel dichloride; sodium t-butanolate;
In
tetrahydrofuran; methanol; dichloromethane; acetic acid methyl ester; acetone; acetonitrile; tert-butyl alcohol; pentane;
DOI:10.1002/(sici)1521-3773(19980202)37:1/2<187::aid-anie187>3.0.co;2-d