Biomedical Engineering Reference
In-Depth Information
SCHEME 9.18
Branching pathway leading to skeletally diverse natural product-like com-
pounds:
148
, NaBH
4
,NH
3
, EtOH, Ti(OEt)
4
then AcOH;
149
, PhNH
2
, TiCl
4
,CH
2
Cl
2
;
150
,
NaH, THF;
151
, SmI
2
(5 equiv), THF/MeOH,
−
78
◦
C;
152
, superhydride, THF or MeLi;
153
,
glycine ethyl ester, DIPEA;
154
,NH
2
OH
·
HCl, NaOAc, MeOH/MeCN, 60
◦
C;
155
, SmI
2
(2
equiv), THF-MeOH,
−
78
◦
C;
156
, MeMgBr;
157
,NH
2
OH
·
HCl, NaOAc, MeCN then toluene,
w, 140
◦
C or 39% PhCl, reflux from
154
;
158
,NH
2
OH
·
HCl, NaOEt, EtOH or 89% NaOEt
from
154
;
159
,NH
2
NHTs toluene, reflux.
