Multi-step reaction with 15 steps
1.1: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - -30 °C
2.1: 35.7 mg / Yb(OTf)3 / CH2Cl2 / 48 h / 20 °C
3.1: 95 percent / NaH / tetrahydrofuran / 0 - 20 °C
4.1: 100 percent / DIBAL-H / tetrahydrofuran / 1 h / 20 °C
5.1: 97 percent / SO3*Py; Et3N / dimethylsulfoxide / 2.5 h
6.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 65 °C
6.2: 100 percent / tetrahydrofuran; hexane / 0.33 h / 0 °C
7.1: liquid NH3; Na / tetrahydrofuran / 0.33 h / -78 °C
7.2: 74 percent / DDQ / benzene / 3.5 h
8.1: ozone / methanol / 0.25 h / -78 °C
8.2: Me2S / methanol / 5 h / -78 °C
9.1: 58.0 mg / pyridine / 16 h
10.1: 17 percent / molecular sieves 4 Angstroem; BF3*Et2O / acetonitrile / 0.17 h / 0 °C
11.1: Jones reagent / acetone / 0.5 h
12.1: 6.3 mg / molecular sieves 4 Angstroem; Et3N; diphenylphosphoryl azide / tetrahydrofuran / 5.5 h / 65 °C
13.1: 78 percent / LiHMDS; DMAP / tetrahydrofuran; CH2Cl2 / -78 - 0 °C
14.1: 93 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C
15.1: BuLi / tetrahydrofuran / 0.25 h / -78 °C
15.2: 50 percent / TMEDA / tetrahydrofuran / 2.5 h / -78 °C
With
pyridine; dmap; n-butyllithium; jones reagent; oxalyl dichloride; pyridine-SO3 complex; 4 A molecular sieve; boron trifluoride diethyl etherate; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; ammonia; sodium; sodium hydride; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; ytterbium(III) triflate;
In
tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; acetone; acetonitrile;
1.1: Swern oxidation / 2.1: cross-aldol reaction / 6.2: Wittig reaction / 7.1: Birch reduction / 11.1: Jones oxidation / 12.1: Cutius rearrangement;
DOI:10.1021/ol052943c