Fukuyama Group - Group Meeting Problems 09/03/2003

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Fukuyama Group - Group Meeting Problems

09/03/2003

1
O
S S
POCl3, Δ ;
HN
N H2O N
H H
O

2
1) acrylonitrile OMe
Triton B 3) OMe 4) methylacrylate
CO2Me
THF, 96% LiClO4
SH
*R
2) mCPBA xylene, reflux , 45% CH2Cl2, rt S
CH2Cl2, 0 °C (diastereoisomer 24%) 88%
O
(= R*SH) 91 %

3
PhI(OCOCF3)2 O
Ph
Ph CO2H CH2Cl2 CO2H

86%

4
O O


N CO2Me
benzene NH
O CO2Me O
50%

5
O Li
C6H13 SiMe3

Et2O, –100 °C
2 h; C6H13
ZrCp2 SiMe3
I2
–100 °C to –30 °C I
1h 60%
Fukuyama Group - Group Meeting Problems
09/17/2003

1) n-BuLi 2) n-BuLi, I2
1 PhS SPh C10H12OS
77% 3) Na2CO3
MeOH LDMAN =
A
83% (2 steps) NMe2 Li

O 3) TMSCN Sn-Bu
1) A, LDMAN cat. ZnI2; O
Sn-Bu
2) aq HBF4 TBAF
64% (2 steps) 59%

2
Ph O
Ph 1) Ph2Cu(CN)Li2
H
THF, –40 °C to rt N
+N OTf– Ph
2) toluene, Δ H
O Ph

3 Ph
H Ph
toluene H
Ph O
O N 110 ºC
O N H
68%
OH

4 O O
OHC OMOM
O
pyrrolidine I
O O O
+
MeCN toluene O O
O reflux
80 °C
O O
2 : 1

5 OMe O OMe
1) O3, CH2Cl2
H –78 °C
MeO
MeO 2) FeSO4 O
Cu(OAc)2 O
OH
Fukuyama Group - Group Meeting Problems
09/24/2003

1 O O

O 1) N2CHCO2Et
S Et2O, 77% CO2H
1) O2 , CH2Cl2; O , 73% 2) HCl, Et2O, 30%
S+ O- C8H10O3
2) O3, CH2Cl2, 64% 3) 20% aq. H2SO4
dioxane, Δ, 38% O

O
2 CO2Me
1) TMSN3, NBS, CH2Cl2
Ph A
2) heptane, reflux
PPh3

H Ph N CO2Et
N A
H H N
toluene Ph
Ph CO2Et reflux
CO2Me

3
1) Ph3P, DEAD
NsNHNH2, THF
Ph OH –10 °C to rt, 2.5 hr
84%
PMP
2) CAN, NaHCO3, MS4A
On-C8H17 TMS Cl(CH2)2Cl-MeCN (3:1 v/v) On-C8H17
40 °C, 10 min; TBAF
91%

4
BnMeN
NMeBn O
Ph CHO S O
N Ph
S +
MeO PhH, reflux * N
O 10 h, 74%
Ph PMP Ph
(* β:α = 7:3)

5 1)
OTMS
O OTMS
mesitylene, 190 °C 3) Collins oxidation O
(in a sealed tube), 63% 92% (in 2 steps)
MeO2C
2) NaBH4(2 eq), MeOH 4) FVT (470 °C, 1.5 torr) O
O rt 75% O
H

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