Biomedical Engineering Reference
In-Depth Information
SCHEME 9.16
Distinct polycyclic scaffolds generated from a common substrate:
112
,
anisole, BF
3
·
Et
2
O, CH
2
Cl
2
,
−
78
◦
C;
113
, 2,4-lutidine, TIPSOTf, then BF
3
·
Et
2
O, CH
2
Cl
2
, 52%;
114
, conc. H
2
SO
4
, toluene, 75%;
115
, SOCl
2
,CH
2
Cl
2
, 59%;
116
,Et
3
SiH, TFA, CH
2
Cl
2
, 80%;
117
,NH
4
F, CH
3
CN, reflux, 67%;
118
, NaCN, CH
3
CN, reflux, 82%;
119
, 3,5-dimethoxyphenol,
BF
3
·
Et
2
O, CH
2
Cl
2
,
−
78
◦
C, 94%;
120
, LiAlH
4
, THF, 0
◦
C, 76%;
121
, PvCl, 1 mol% DMAP,
Et
3
N, CH
2
Cl
2
, 81%.
