Multi-step reaction with 18 steps
1: 88 percent / Et3N imidazole
2: 92 percent / pyridine
3: 1.) LDA, 2.) TBSCl, HMPA, 4.) aq. K2CO3 / 1.) THF, -78 deg C, 3.) -78 deg C to room temperature, 4.) THF
5: LiAlH4
6: Et3N, DMAP
7: 94 percent / CuCN / 0 °C
8: m-CPBA
9: (MeO)3P / methanol
10: Et3N
11: H2SO4 / tetrahydrofuran
12: 96 percent / TPAP, NMO
13: 56 percent
14: 95 percent / DIBALH
15: 100 percent / TPAP, NMO
16: KOt-Bu
17: TBAF / tetrahydrofuran
18: 1.) catecholborane, N,N-diethylaniline, 2.) TPPTS, i-Pr2NH / 2.) Pd(OAc)2 / 2.) MeCN, H2O
With
pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; sulfuric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; trisodium tris(3-sulfophenyl)phosphine; diisobutylaluminium hydride; potassium carbonate; tert-butyldimethylsilyl chloride; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; N,N-diethylaniline; lithium diisopropyl amide; phosphorous acid trimethyl ester; benzo[1,3,2]dioxaborole;
palladium diacetate;
In
tetrahydrofuran; methanol;
DOI:10.1021/jo9813742