Multi-step reaction with 13 steps
1.1: 93 percent / L-proline / dimethylformamide / 24 h / 0 °C
2.1: 90 percent / H2 / Pd/C / tetrahydrofuran / 3 h
3.1: 68 percent / Et3N / 2.5 h / 0 °C
4.1: 72 percent / DIBAL-H / diethyl ether / -60 - -30 °C
5.1: DIBAL-H / CH2Cl2 / 0.33 h / -50 - -30 °C
6.1: Amberlyst 15 / tetrahydrofuran / 48 h / 60 °C
7.1: Et3N; DMAP / CH2Cl2
8.1: t-BuLi; Me2Zn / tetrahydrofuran
8.2: tetrahydrofuran / 2 h / -78 - -40 °C
9.1: Et3N / tetrahydrofuran / 1 h / -40 - -20 °C
10.1: dimethyldioxirane / acetone / -90 °C
10.2: 74 percent / TBAF / tetrahydrofuran
11.1: 71 percent / Et3N / CH2Cl2
12.1: tert-butylhydroperoxide; VI(acac)2 / CH2Cl2
12.2: 75 percent / K2CO3 / methanol
13.1: 62 percent / NaBH4 / methanol / -50 - -10 °C
With
tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; Amberlyst 15; VI(acac)2; hydrogen; dimethyl zinc(II); tert.-butyl lithium; 3,3-dimethyldioxirane; diisobutylaluminium hydride; triethylamine; L-proline;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone;
8.2: Michael addition;
DOI:10.1002/anie.200502826