Multi-step reaction with 12 steps
1.1: 89 percent / TBTU; DIPEA / dimethylformamide / 20 °C
2.1: 69 percent / 2-(di-tert-butylphosphanyl)biphenyl; Ag3PO4 / Pd2(dba)3 / tetrahydrofuran / 90 °C
3.1: 97 percent / DEAD; PPh3 / tetrahydrofuran
4.1: aq. OsO4; DMAP / 2-methyl-propan-2-ol / 20 °C
4.2: H2S / tetrahydrofuran / -50 °C
5.1: 90 percent / p-TsOH / toluene / 1 h / 95 °C
6.1: TBTU; DIPEA / dimethylformamide
7.1: p-TsOH / 95 °C
8.1: 85 percent / NaBH4 / methanol; tetrahydrofuran / -10 °C
9.1: 81 percent / (+)-10-camphorsulfonic acid / benzene / 6.5 h / 60 °C
10.1: AlMe3
10.2: 88 percent / toluene; CH2Cl2 / 20 °C
11.1: 95 percent / pyridine / CH2Cl2 / 0 °C
12.1: aq. DDQ / tetrahydrofuran / 20 °C
12.2: PPh3; Et3N; (CCl3)2 / CH2Cl2 / 20 °C
With
pyridine; dmap; sodium tetrahydroborate; osmium(VIII) oxide; silver orthophosphate; trimethylaluminum; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; toluene-4-sulfonic acid; (+)-10-camphorsulfonic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; johnphos; diethylazodicarboxylate;
tris(dibenzylideneacetone)dipalladium (0);
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene;
1.1: Acylation / 2.1: Dehydroiodination / 3.1: Etherification / 4.1: Oxidation / 4.2: Substitution / 5.1: Hydrolysis / 6.1: Acylation / 7.1: Rearrangement / 8.1: Reduction / 9.1: Cyclization / 10.1: Metallation / 10.2: Acylation / 11.1: Acetylation / 12.1: Oxidation / 12.2: Dehydration;
DOI:10.1002/(SICI)1521-3773(20000303)39:5<937::AID-ANIE937>3.0.CO;2-A