Multi-step reaction with 7 steps
1.1: (S,S)-2-nBu-4,5-(CONMe)2-1,3,2-dioxaborolan; Et2Zn / 1,2-dimethoxy-ethane
2.1: 100 percent / NaH / dimethylformamide / 12 h / 0 - 25 °C
3.1: O3 / CH2Cl2; methanol / -78 °C
3.2: 83 percent / NaBH4 / CH2Cl2; methanol / 1 h / -78 - 25 °C
4.1: Et3N / CH2Cl2 / 1 h / 25 °C
5.1: NaI / acetone / 12 h / 25 °C
6.1: LDA / tetrahydrofuran / 6 h / 0 °C
6.2: 87 percent / tetrahydrofuran / 14 h / -98 - -10 °C
7.1: MeI / 3 h / Heating
7.2: 91 percent / 3N HCl / pentane / 3 h / 25 °C
With
(S,S)-2-nBu-4,5-(CONMe)2-1,3,2-dioxaborolan; diethylzinc; sodium hydride; ozone; triethylamine; sodium iodide; lithium diisopropyl amide; methyl iodide;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1002/anie.200351819