Fukuyama Group - Group Meeting Problems

12/04/2002

1
OAc
SMe
OH
Me2S SMe
OMe BF4 reflux
N O bycyclic N
compound toluene
O
O

2 O
O Ph Ph2S2, AIBN
Ph
O Ph PhCl, hν, reflux
52%
Ph

3
CpW(CO)3
O O O
TfOH Tungsten-contained 1) (CO2H)2, 75%
ethyl ester O
OEt EtOH-CH2Cl2 2) NOBF4, LiCl
CH3CN, 47% H
OEt 65%

4
O O
HgCl2 LiPdCl3, CH3CN, 0 ºC to rt;
COOH A
K2CO3, reflux CHCl
23% 59%

5
Cl
R (CH2O)n, AlCl3 (0.5 eq)
R
R' CH2Cl2, rt, 2 h; H2O R'
O
62%
 Fukuyama Group - Group Meeting Problems
12/18/2002

1
1) TIPSOTf, i-Pr2NEt
O Et2O-Hex TMSCHN2 Sii-Pr3
N2 0 °C to rt CH2Cl2-Hex, rt;
A
2) hυ SiO2, rt O
benzene

1) MeO OMe
2 1) TFA OMe
Cr(CO)5 MeO OMe THF-H2O O
98% 85% NHt-Bu
MeO Tricyclic compound O
2) t-BuNC 2) MeOH
THF 100 °C MeO
85% 92%

NaCH2S(O)CH3 CHO
S
O2
NO2 THF-DMSO
rt

Bu
4 Cl
Pd(PPh3)4
N
(1 mol%)
N
Bu
THF, rt Cl

85%

5
1) NCS, Et2O
O O
2) cat CuCl, CuCl2 Me N
MeHN aq AcOH-THF

3) aq HCl, MeOH O
4) toluene, reflux
 Fukuyama Group - Group Meeting Problems
12/25/2002

1
MeO 1) Bu3SnTMS, CsF 2) PPA, 60 ºC MeO
N DMF, rt 40 h, 66%
H N
MeO MeO
OHC 8 h, 85%
I PPA=polyphosphic acid

2
O
NaN3 (ca. 5 eq) O
O
N
MeCN/H2O (3:1) O
Cl
rt, 5 min
97%

3
2) MeOTf
1) BuLi benzene, 0 °C Me
N ether, –20 °C; 96% Me
S
S SiMe3 Me
3) CsF
DMSO, rt; MeO CH2SMe
MeO CH2Br
aqNaOH, 68%
58%

4
N3 H H
H Bn2NH, AcOH Pd(OH)2/C, H2 N
HO O OH HO NH2
EtOH, 40 °C MeOH
HO OH HO OH

5
O O
(TMS)3SiH
Me
AIBN
H
N3 NH