Multi-step reaction with 10 steps
1.1: 95 percent / diethyl ether / 0 - 25 °C
2.1: LDA / tetrahydrofuran / 0 °C
2.2: 86 percent / tetrahydrofuran / -120 - 25 °C
3.1: O3 / CH2Cl2 / -78 °C
4.1: CH2Cl2 / 25 °C
5.1: 96 percent / AD-mix β; aq. MeSO2NH2 / 2-methyl-propan-2-ol / 0 °C
6.1: p-toluenesulfonic acid / 25 °C
7.1: 95 percent / LAH / diethyl ether / 0 °C
8.1: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / -40 - -30 °C
9.1: t-BuLi; DMPU / tetrahydrofuran / -78 °C
9.2: tetrahydrofuran / -78 - 25 °C
10.1: 94 percent / H2 / Lindlar catalyst / methanol / 25 °C
With
1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium aluminium tetrahydride; 2,6-di-tert-butyl-4-methylpyridine; methanesulfonamide; hydrogen; tert.-butyl lithium; toluene-4-sulfonic acid; ozone; 1,4-bis(9-O-dihydroquinidine)phthalazine; lithium diisopropyl amide;
Lindlar's catalyst;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; tert-butyl alcohol;
4.1: Wittig olefination / 5.1: Sharpless asymmetric dihydroxylation / 10.1: Lindlar reduction;
DOI:10.1055/s-2003-42071