Biomedical Engineering Reference
In-Depth Information
SCHEME 1.4
Twelve-fold branching strategy employed by Robbins et al. (a) NH
2
OH
···
HCl, NaOAc, MeCN then toluene 140
◦
C,
w;
(b) NH
2
OH
···
HCl, NaOAc, MeCN, 60
◦
C; (c) NH
2
OH
···
HCl, NaOEt, EtOH; (d) NaBH
4
,NH
3
, EtOH, Ti(OEt)
4
then AcOH; (e) PhNH
2
, TiCl
4
,
CH
2
Cl
2
, rt; (f) DIPEA, H
2
NCH
2
CO
2
Et; (g) NH
2
NHTs, toluene, reflux; (h) NaH, THF; (i) SmI
2
(2 equiv), THF, MeOH,
−
78
◦
C; (j) SmI
2
(5 equiv),
THF, MeOH,
−
78
◦
C; (k) superhydride, THF; (l) MeMgBr, THF. (From [56], with permission of The Royal Society of Chemistry.)
