Fukuyama Group - Group Meeting Problems 01/09/2007
Fukuyama Group - Group Meeting Problems 01/09/2007
Fukuyama Group - Group Meeting Problems 01/09/2007
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1<br />
2<br />
3<br />
4<br />
5<br />
MeO<br />
<strong>Fukuyama</strong> <strong>Group</strong> - <strong>Group</strong> <strong>Meeting</strong> <strong>Problems</strong><br />
<strong>01</strong>/<strong>09</strong>/<strong>2007</strong><br />
OH<br />
N<br />
Ph<br />
O<br />
OEt<br />
n-Pr<br />
O<br />
N<br />
CuCl, NaOt-Bu<br />
(R,R)-BDPP<br />
PhH, rt<br />
95% (dr=4:1)<br />
O<br />
MeO N<br />
Br<br />
Me N CO2Me Ph<br />
Me<br />
H<br />
NaI (excess)<br />
acetone, rt<br />
60%<br />
SiH 2t-Bu CO<br />
O<br />
O O -<br />
1) mCPBA<br />
CH 2Cl 2<br />
quant.<br />
2) Ac 2O, Δ<br />
83%<br />
S +<br />
Et<br />
CO 2Me<br />
1) K 2CO 3<br />
MeOH<br />
2) SOCl 2<br />
Py, 99%<br />
[Rh(acetone) 2-<br />
(P(OPh) 3) 2)]BF 4<br />
PhH, 60 ºC<br />
CSA<br />
toluene<br />
reflux<br />
98%<br />
toluene, reflux<br />
97%<br />
PtCl 2 (3 mol%)<br />
toluene<br />
reflux<br />
89%<br />
NaH<br />
THF<br />
reflux<br />
99%<br />
C 15H 14NO 2Cl<br />
EtO 2C<br />
N<br />
Ph<br />
M. J. S. Dewar et al., J. Org. Chem., 40, 1521 (1975)<br />
MeLi (2 eq)<br />
Et 2O, rt<br />
56% (2 steps)<br />
N<br />
O<br />
OH TBS<br />
OH<br />
n-Pr<br />
J. L. Leighton et al., Org. Lett., 5, 3535 (2003)<br />
O<br />
G. Dyker et al., Chem. Commun., 2260 (2006)<br />
NaIO 4<br />
MeOH-H 2O;<br />
heat<br />
90%<br />
O<br />
MeO<br />
MeO<br />
H<br />
N<br />
O<br />
MeO2C A. Padwa and M. D. Danca, Org. Lett., 4, 715 (2002)<br />
1)<br />
N<br />
CN<br />
DMSO, 60 °C<br />
93%<br />
2) t-BuOK, HMPA<br />
THF-DMSO<br />
–30 °C<br />
NC<br />
Me N CO2Me N<br />
Ph<br />
Me<br />
S. M. Weinreb et al., J. Org. Chem., 43, 125 (1978)
1<br />
2<br />
3<br />
4<br />
5<br />
Br<br />
O<br />
<strong>Fukuyama</strong> <strong>Group</strong> - <strong>Group</strong> <strong>Meeting</strong> <strong>Problems</strong><br />
<strong>01</strong>/17/<strong>2007</strong><br />
O<br />
N<br />
H<br />
O<br />
O<br />
N<br />
OEt<br />
CHO<br />
NH 2<br />
O<br />
H<br />
1) DIBAL (1.1 eq)<br />
THF, –78 ºC;<br />
BrMg<br />
62%<br />
Ph<br />
Ph (1 eq)*<br />
Pb(OAc) 4 (1 eq)<br />
CH 2Cl 2, rt, 30 min<br />
39-51%<br />
A (1 eq)*<br />
CH 2Cl 2, 0 °C, 2 h<br />
(no purification)<br />
TMS<br />
2) TPAP, NMO (2 eq)*<br />
CH 2Cl 2<br />
58%<br />
(*theoretical amount)<br />
NH<br />
N<br />
c-Hex<br />
Ph 2O<br />
reflux<br />
70%<br />
t-BuOCl (1.0 eq)<br />
NEt 3 (1.2 eq)<br />
THF<br />
−78 °C to rt<br />
1) MeNO 2, Et 3N<br />
THF-EtOH<br />
rt, 85%<br />
2) TMSCl, Et 3N<br />
THF, rt, 84%<br />
H 2NNH 2•HCl<br />
EtOH, 45 °C, 40 min<br />
75%<br />
PhH, reflux, 3 h<br />
37% (2 steps)<br />
OEt<br />
A (C 14H 14N 2)<br />
(*theoretical amount)<br />
A. Padwa et al., J. Am. Chem. Soc., 1993, 115, 2637<br />
C 12H 20O 2Si<br />
CDCl 3, rt<br />
60% (2 steps)<br />
3) PhNCO, Et 3N<br />
1,5-hexadiene (xs)<br />
PhH, reflux, 74%<br />
4) ICl, CH 2Cl 2<br />
–78 °C, 53%<br />
1) mCPBA<br />
CH 2Cl 2<br />
88%<br />
2) 70% HClO 4<br />
THF-H 2O<br />
CHO<br />
H<br />
K. Inomata et al., Org. Lett., 2004, 6, 4<strong>09</strong><br />
Br<br />
T. Lindel et al., Org. Lett., 9, 283 (<strong>2007</strong>)<br />
NC<br />
N. E. Schore and M. J. Kurth et al., J. Org. Chem., 1995, 60, 4196<br />
1) Br 2, CH 2Cl 2, 0 °C, 20 min<br />
2) KCN, THF-H 2O (1:1), rt, 4 h<br />
3) NaH, DMF, 40 °C, 6 h<br />
77% (3 steps)<br />
NC<br />
O<br />
N<br />
c-Hex<br />
N. De Kimpe et al., Tetrahedron Lett., 20<strong>01</strong>, 42, 3921<br />
H<br />
I<br />
N<br />
O<br />
N<br />
O
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