Multi-step reaction with 14 steps
1.1: 88 percent / 2,6-lutidine / CH2Cl2 / -40 - 25 °C
2.1: tetrahydrofuran / -78 °C
2.2: NaBO3*4H2O; H2O / tetrahydrofuran / 12 h / 25 °C
3.1: 88 percent / 2,6-lutidine / CH2Cl2 / -40 - 25 °C
4.1: O3 / CH2Cl2 / -78 °C
4.2: 92 percent / PPh3 / CH2Cl2 / 12 h / -78 - 25 °C
5.1: 87 percent / LDA / tetrahydrofuran / 1 h / -78 - -20 °C
6.1: 93 percent / H2 / Lindlar catalyst / methanol / 12 h / 25 °C
7.1: 94 percent / K2CO3 / methanol / 3.5 h / 25 °C
8.1: TBAF
9.1: 2,6-lutidine
10.1: 87 percent / TBAF / tetrahydrofuran / 48 h / 45 °C
11.1: 69 percent / NBS; AgNO3 / acetone / 0.5 h / 25 °C
12.1: 98 percent / 1 h / 25 °C
13.1: n-Bu3SnH; Ph3P / Pd2(dba)3*CHCl3 / 0.5 h / 25 °C
13.2: AsPh3; iPr2NEt / Pd2(dba)3*CHCl3 / dimethylformamide / 10 h / 35 °C
14.1: TBAF / tetrahydrofuran / 2 h / 25 °C
With
2,6-dimethylpyridine; N-Bromosuccinimide; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; potassium carbonate; ozone; silver nitrate; triphenylphosphine; lithium diisopropyl amide;
tris(dibenzylideneacetone)dipalladium(0) chloroform complex; Lindlar's catalyst;
In
tetrahydrofuran; methanol; dichloromethane; acetone;
1.1: Etherification / 2.1: Addition / 2.2: Hydrolysis / 3.1: Etherification / 4.1: Oxidation / 4.2: Reduction / 5.1: Condensation / 6.1: Catalytic hydrogenation / 7.1: Substitution / 8.1: Substitution / 9.1: Etherification / 10.1: Substitution / 11.1: Bromination / 12.1: Etherification / 13.1: Metallation / 13.2: Intramolecular Stille reaction / 14.1: Substitution;
DOI:10.1002/(SICI)1521-3773(19990816)38:16<2447::AID-ANIE2447>3.0.CO;2-O