Fukuyama Group - Group Meeting Problems

07/17/2011
1
O

O HO

BF4
+

PhI

Me

KOCEt3 (3 eq)

[Fe2(CO)9]* (2 eq)
benzene
95 C;

THF
78 C to rt

DBU (20 eq)

95 C

74%

O O

51%
* low yield under basic condition

E. M. Carreira et al., Angew. Chem. Int. Ed., 50, 2962 (2011)

2
O
Dy(OTf)3

PhHN

CH3CN, 80 C

OH

PhN

90%

J. R. Alaniz et al., Angew. Chem. Int. Ed., 50, 7167 (2011)

3
Me
N

Ph
O

CO2H

TFAA (3 eq*)

Ph3PEtBr
n-BuLi, THF

AcOEt
0 C to rt

20 C to rt;
AcOH, 80 C

87%
(* theoretically 2 eq)

87%

Me
Ph

CF3
N
Me

M. Kawase et al., Org. Lett., 12, 4776 (2010)

4
SiMe3

Boc

BocNHOH (2.5 eq)

NaIO4 (2.5 eq)

OsO4, NMO

SmI2

HO

MeOH/ H2O
20 C

THF/ t-BuOH/ H2O

20 C

THF
78 C

HO

52%

82%

60%

NH OH
*1 OH
H
NBoc
OH OH

*1 stereochemistry
not determined

Y. Landais et al., Org. Lett., 10, 4195 (2008)

Fukuyama Group - Group Meeting Problems

07/24/2011
1
H H H O
MeO

BHT, PhH
H

235 C, 88%
H
O

1) MeMgBr, CuBrMe2S
Me2S, THF, 20 C
66%, 14:1 dr

H O
BHT, PhH

MeO

120 C, 96%

2) TMSCHN2
MeOH/PhH, rt, 93%

H
CO2Me
Me

M. L. Snapper et al., Org. Lett., 3, 2819 (2001)

O

2
O

[Rh(OCOC7H15)2]2 (cat.)
DMAD

N2

MeO2C

CH2Cl2
rt

MeO2C

H
N

70%

A. Padwa et al., Tetrahedron Lett., 34, 7853 (1993)

HO
LTA
CHCl3
-40 C

Tricyclic Compound
(C17H24O3)

1) CrO3
H2SO4/H2O/acetone
rt, 96%
2) OsO4, THF
rt, 79%

O
O

3) p-TsOHH2O
toluene, reflux
85%

61%
T. R. R. Pettus et al., J. Am. Chem. Soc., 133, 1603 (2011)

4
Ph
O

Ph
O

NIS (2.5 eq)

H2O (5.0 eq)
MeCN
40 to 0 C
62%*

1) DDQ
MeCN-H2O (10:1)
60 C
58% (36% SM)

CAN
MeCN-H2O (1:1)
rt;

2) NaH2PO4, NaClO2
2-methyl-2-butene
t-BuOH-H2O (5:1), rt
92%

K2CO3

O
I

O
O

80%

(*18% other diastereomixture)

Y. Kita et al., Angew. Chem. Int. Ed., 44, 734 (2005)

Fukuyama Group - Group Meeting Problems

07/31/2011
1
O

N2

O
N
Me

1) allyl alcohol
Rh2(OAc)4
CH2Cl2, rt

3) H(OH)NMeHCl
pyridine, MeOH
reflux

2) xylenes
reflux
85% (2 steps)

4) imidazoleHCl
EtOH, reflux
81% (2 steps)

O
MeN

H
O

N
Me

J. L. Wood et al., Tetrahedron, 66, 6647 (2010)

2
OH
NMe
OAc
N
H

OH

NMe

N
H

TFA, rt
61%

* : Diastereomixture
S. Blechert et al., J. Am. Chem. Soc., 126, 3534 (2004)

3
O

OH

O
Br
MeO2C

Pd(PPh3)4, i-Pr2NH
microwave
benzene
160 C
60%

1) DMP
CH2Cl2, rt
77%

O O

O
O

2) cat. RuCl3, NaIO4

CCl4-CH3CN-H2O
50%

CO2Me

J. Suffert et al., Angew. Chem. Int. Ed., 50, 3285 (2011)

TBSO

SmI2, HMPA
N
Me

i-PrOH
THF, 35 C
99%

1) CsF, PhN(Tf)2
DME
2) Pd(OAc)2, PPh3
HCO2H, DMF
87% (2 steps)

O
LDA
THF, 78 C;
MeI

NMe

Me

67%

Y. Landais et al., Org. Lett., 10, 4441 (2008)