Multi-step reaction with 14 steps
1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 °C
1.2: 1 h / 50 °C
2.1: dimethylsulfide borane complex / tetrahydrofuran / 0 - 20 °C
2.2: 0 - 20 °C
3.1: diisobutylaluminium hydride / hexane; dichloromethane / 0 - 20 °C
3.2: 2.5 h
4.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C
5.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 19 h / 20 °C / Molecular sieve
6.1: zinc trifluoromethanesulfonate / tetrahydrofuran / 20 °C
7.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 20 °C
7.2: 15 h
8.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / -78 °C
9.1: n-heptane; dichloromethane / -78 - 0 °C
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C
11.1: 2,6-dimethylpyridine / dichloromethane / -78 °C
12.1: dimethyl sulfoxide / 3 h / 20 - 80 °C
13.1: diethyl ether / -78 - 0 °C
14.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / 0 °C
14.2: 0.33 h / -78 °C
With
1H-imidazole; 2,6-dimethylpyridine; n-butyllithium; tetrapropylammonium perruthennate; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; diethyl ether; hexane; n-heptane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; mineral oil;
1.2: Suzuki-Miyaura coupling / 14.2: Aldol condensation;
DOI:10.1021/ol102925d