Fukuyama Group - Group Meeting Problems 07/17/2011
Fukuyama Group - Group Meeting Problems 07/17/2011
Fukuyama Group - Group Meeting Problems 07/17/2011
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1<br />
2<br />
3<br />
4<br />
O<br />
O<br />
Ph<br />
<strong>Fukuyama</strong> <strong>Group</strong> - <strong>Group</strong> <strong>Meeting</strong> <strong>Problems</strong><br />
<strong>07</strong>/<strong>17</strong>/<strong>2011</strong><br />
O<br />
H<br />
Me<br />
PhHN<br />
O<br />
+<br />
Me<br />
N<br />
PhI<br />
BF 4<br />
CO 2H<br />
O<br />
OH<br />
KOCEt 3 (3 eq)<br />
THF<br />
–78 °C to rt<br />
TFAA (3 eq*)<br />
AcOEt<br />
0 °C to rt<br />
74%<br />
87%<br />
(* theoretically 2 eq)<br />
SiMe 3 BocNHOH (2.5 eq)<br />
NaIO 4 (2.5 eq)<br />
MeOH/ H 2O<br />
20 °C<br />
52%<br />
[Fe 2(CO) 9]* (2 eq)<br />
benzene<br />
95 °C;<br />
DBU (20 eq)<br />
95 °C<br />
51%<br />
* low yield under basic condition<br />
Ph 3PEtBr<br />
n-BuLi, THF<br />
–20 °C to rt;<br />
AcOH, 80 °C<br />
87%<br />
Ph<br />
Me<br />
O<br />
N<br />
Me<br />
O O<br />
E. M. Carreira et al., Angew. Chem. Int. Ed., 50, 2962 (<strong>2011</strong>)<br />
Dy(OTf) 3<br />
CH 3CN, 80 °C<br />
90%<br />
J. R. Alaniz et al., Angew. Chem. Int. Ed., 50, 7167 (<strong>2011</strong>)<br />
OsO 4, NMO<br />
THF/ t-BuOH/ H 2O<br />
20 °C<br />
82%<br />
CF 3<br />
M. Kawase et al., Org. Lett., 12, 4776 (2010)<br />
SmI 2<br />
THF<br />
–78 °C<br />
60%<br />
O<br />
PhN<br />
HO<br />
HO<br />
Boc<br />
Y. Landais et al., Org. Lett., 10, 4195 (2008)<br />
H<br />
NH<br />
OH<br />
OH<br />
* OH<br />
NBoc<br />
OH<br />
1<br />
H<br />
* 1 stereochemistry<br />
not determined
1<br />
MeO<br />
2<br />
3<br />
4<br />
H<br />
HO<br />
H<br />
O<br />
<strong>Fukuyama</strong> <strong>Group</strong> - <strong>Group</strong> <strong>Meeting</strong> <strong>Problems</strong><br />
<strong>07</strong>/24/<strong>2011</strong><br />
H H O H<br />
O<br />
O<br />
LTA<br />
N 2<br />
CHCl 3<br />
-40 °C<br />
61%<br />
BHT, PhH<br />
235 ºC, 88%<br />
O<br />
Ph Ph NIS (2.5 eq)<br />
O O<br />
H2O (5.0 eq)<br />
MeCN<br />
–40 to 0 °C<br />
N<br />
62%*<br />
Tricyclic Compound<br />
(C <strong>17</strong>H 24O 3)<br />
(*18% other diastereomixture)<br />
1) MeMgBr, CuBr•Me 2S<br />
Me 2S, THF, –20 ºC<br />
66%, 14:1 dr<br />
2) TMSCHN 2<br />
MeOH/PhH, rt, 93%<br />
[Rh(OCOC 7H 15) 2] 2 (cat.)<br />
DMAD<br />
CH 2Cl 2<br />
rt<br />
70%<br />
1) DDQ<br />
MeCN-H 2O (10:1)<br />
60 °C<br />
58% (36% SM)<br />
2) NaH 2PO 4, NaClO 2<br />
2-methyl-2-butene<br />
t-BuOH-H 2O (5:1), rt<br />
92%<br />
BHT, PhH<br />
120 ºC, 96%<br />
MeO<br />
H<br />
Me<br />
H<br />
O<br />
CO 2Me<br />
M. L. Snapper et al., Org. Lett., 3, 2819 (2001)<br />
MeO 2C<br />
MeO 2C<br />
O<br />
O<br />
N<br />
A. Padwa et al., Tetrahedron Lett., 34, 7853 (1993)<br />
1) CrO 3<br />
H 2SO 4/H 2O/acetone<br />
rt, 96%<br />
2) OsO 4, THF<br />
rt, 79%<br />
3) p-TsOH⋅H 2O<br />
toluene, reflux<br />
85%<br />
H<br />
O<br />
O O O<br />
T. R. R. Pettus et al., J. Am. Chem. Soc., 133, 1603 (<strong>2011</strong>)<br />
CAN<br />
MeCN-H 2O (1:1)<br />
rt;<br />
K 2CO 3<br />
80%<br />
O O<br />
Y. Kita et al., Angew. Chem. Int. Ed., 44, 734 (2005)<br />
I<br />
O
1<br />
2<br />
3<br />
4<br />
O<br />
O<br />
TBSO<br />
N 2<br />
O<br />
<strong>Fukuyama</strong> <strong>Group</strong> - <strong>Group</strong> <strong>Meeting</strong> <strong>Problems</strong><br />
<strong>07</strong>/31/<strong>2011</strong><br />
N<br />
Me<br />
N<br />
H<br />
*<br />
OH<br />
OH<br />
* : Diastereomixture<br />
O<br />
O<br />
Br<br />
MeO2C N<br />
Me<br />
I<br />
OH<br />
1) allyl alcohol<br />
Rh 2(OAc) 4<br />
CH 2Cl 2, rt<br />
2) xylenes<br />
reflux<br />
85% (2 steps)<br />
NMe<br />
OAc<br />
Pd(PPh 3) 4, i-Pr 2NH<br />
microwave<br />
benzene<br />
160 °C<br />
60%<br />
SmI 2, HMPA<br />
i-PrOH<br />
THF, –35 °C<br />
99%<br />
TFA, rt<br />
61%<br />
3) H(OH)NMe⋅HCl<br />
pyridine, MeOH<br />
reflux<br />
O<br />
MeN<br />
4) imidazole⋅HCl<br />
H<br />
EtOH, reflux<br />
O<br />
81% (2 steps) N<br />
Me<br />
J. L. Wood et al., Tetrahedron, 66, 6647 (2010)<br />
S. Blechert et al., J. Am. Chem. Soc., 126, 3534 (2004)<br />
1) DMP<br />
CH 2Cl 2, rt<br />
77%<br />
2) cat. RuCl 3, NaIO 4<br />
CCl 4-CH 3CN-H 2O<br />
50%<br />
N<br />
H<br />
O<br />
O<br />
O<br />
H<br />
O<br />
O<br />
NMe<br />
O O<br />
CO 2Me<br />
J. Suffert et al., Angew. Chem. Int. Ed., 50, 3285 (<strong>2011</strong>)<br />
1) CsF, PhN(Tf) 2<br />
DME<br />
2) Pd(OAc) 2, PPh 3<br />
HCO 2H, DMF<br />
87% (2 steps)<br />
LDA<br />
THF, –78 °C;<br />
MeI<br />
67%<br />
Me<br />
O<br />
NMe<br />
Y. Landais et al., Org. Lett., 10, 4441 (2008)