Multi-step reaction with 15 steps
1.1: HF*pyr; pyridine / tetrahydrofuran / 72 h
2.1: 65 percent / DMAP / CH2Cl2 / 10 °C
3.1: 62 percent / 1,4-cyclohexadiene / 10 percent Pd/C / ethyl acetate
4.1: i-PrNEt2 / benzene
5.1: 81 percent / DMAP / benzene
6.1: PPTS; HC(OCH3)3 / methanol; CH2Cl2 / -30 °C
7.1: 66 percent / Dess-Martin periodinane; pyridine / CH2Cl2
8.1: NaHMDS / tetrahydrofuran / -78 °C
8.2: 75 percent / tetrahydrofuran / -15 °C
9.1: KHMDS / tetrahydrofuran / -78 °C
9.2: tetrahydrofuran / -78 °C
10.1: 54 percent / Et3NSO2NCO2Me / benzene
11.1: (R)-2-methyl-CBS-oxazaborolidine; BH3*SMe2 / CH2Cl2
11.2: MeOH / CH2Cl2
11.3: 89 percent / pyridine; DMAP
12.1: aq. PPTS / tetrahydrofuran
13.1: Na2CO3; MeOH
14.1: 80 percent / aq. p-TsOH / acetonitrile
15.1: 62 percent / DIC; DMAP / CH2Cl2 / 23 °C
With
pyridine; methanol; dmap; Burgess Reagent; N,N-diethyl-N-isopropylamine; cyclohexa-1,4-diene; dimethylsulfide borane complex; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; pyridine hydrogenfluoride; dacarbazine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; trimethyl orthoformate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetonitrile; benzene;
1.1: Cyclization / 2.1: silylation / 3.1: debenzylation / 4.1: Esterification / 5.1: Cyclization / 6.1: desilylation / 7.1: Oxidation / 8.1: Metallation / 8.2: Substitution / 9.1: Metallation / 9.2: Substitution / 10.1: Dehydration / 11.1: Reduction / 11.2: protonation / 11.3: Acylation / 12.1: Hydrolysis / 13.1: saponification / 14.1: Hydrolysis / 15.1: Esterification;
DOI:10.1021/ja990860j