有机化学习题福山组会题2005年104
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1
5
2
3
4
O O O
N 2
O
1) Rh 2(OAc)4 (3 mol%), CH 2Cl 2, 74%2) 6 N HCl, 1,4-dioxane, 93%3) MeI, NaH, DMF, 75%4) sealed tube
1-methylcyclohexene, 150 °C, 62%
O
O
Me H
OMe
J. E. Baldwin et al . Org . Lett . 1, 1933 (1999)
N S AcO
CO 2CH 3
Et Me
O
K 2CO 3
MeOH-H 2O
TsOH·H 2O toluene reflux 76%
N
S
Et CO 2CH 3
H.-G. Hahn et al . Heterocycles, 57, 1697 (2002)
O
OMe
NO 2Me
Me Me Me
OMe
O
H 2N O Me Me
Me
Me Boc 2O DMAP benzene-MeCN
Raney Ni H 2MeOH
tricyclo compound
D. G. J. Young et al . J. Org. Chem. 67, 3134 (2002)
OH H Me
1) Bu 3SnH (1.2 eq) AIBN (cat) PhH, 80 °C 2) TBAF, THF
81% (2 steps)
O
Me 3Si
Br
Tsai, Y. M. et al ., Tetrahedron Lett . 34, 1303 (1993)
O
O Ph
O Ph
OTMS
C 29H 40O 6SSi
∗
∗
∗
O Ph
O
O
O
Ph C 26H 32O 4
Stereochemistry C*?
"H +"C 21H 22O 3
SO 2, toluene Tf 2NH (cat.)
P. Vogel et al., Chem. Eur. J .,11,465 (2005)
78% d.r. 5:1
C 8H 18OSi
1
5
2
3
4
O H
1) TrisNHNH 2, THF;
t -BuLi (theoretically 2 eq),–78 °C;
, 36%
2) µwave, THF, 110°C; air, 80%3) µwave, toluene, 150 °C, 61%
O
O
t -BuO
H
O O
O t -Bu
H
D. C. Harrowven et al., Angew. Chem. Int. Ed. 44, 1221 (2005)
1) Ph 3P=C=C=O THF,reflux, 16h 60%
2) PhMe, 180 °C, 24h (sealed glass tube) 65%3) O 2 (air)
Rainer, Schobert. et al ., Tetrahedron Lett . 42, 4561 (2001)
HO
O
O
O
O O O
OH
N 3
Me
Ph
toluene, 100 °C;
TMSCN
NH H CN Ph
Me
K. S. Feldman et al., J. Am. Chem. Soc., 127, 4590 (2005)
OH
O
HO
1) SeO 2 TBHP CH 2Cl 22) AllylBr NaH THF
3) DBU (2.0 eq) toluene 220 ºC µwave 75%
L. Barriault etal., Org. Lett. 4, 1371 (2002)
H
O
O
CO 2Me
O
O
H
Co 2(CO)8, 4Å MS toluene;Me 3NO•2H 2O toluene
K 2CO 3MeOH
J.D. Winkler et al., Org. Lett. 7, 1489 (2005)
1
5
2
3
4
TBS
Ph
O O
TBSO
HO
Ph
NHMDS HMPA/THF –80 ºC to rt, 2 h
43%
K. Takeda et al., 125th Nihon Yakugakukai Abstract 4, 118 (2005)
N Boc
BocN
Ts
HO
Ts
I
HO
Bu 3SnH Et 3B, O 2CH 2Cl 20 °C 78%
80 °C 82%
D. H. Hodgson et al., Org. Lett. 7, 815 (2005)
O
O
OH
CyNC DMAD
PhH reflux 68%
O
O
O
NHCy
CO 2Me
CO 2Me
V. Nair et al., Heterocycles 58, 147 (2002)H
O OBn
C 9H 10O 2
D-Proline DMF,r.t.98% e.e.anti:syn 4:178%
C 18H 20O 4
TMSO OR MgBr 2.OEt 2
65%,d.r. 10:1
R=p-benzyloxy cinnamoyl
O BnO HO
OR
OBn
OH
C 21H 24O 4Si Protected D-Glucopyranose Stereoselectivities?
D. W. C. MacMillan et al., J. Am. Chem. Soc. 127, 3696 (2005)
S
S S Cl Cl
CO 2Me
MeO 2C (DMAD)
xylene, rt quant
DMAD xylene, reflux 55% (1:1)
S
S S
R
R
R
R +
S
S
R
R
R
S R
R = CO 2Me
V. A. Ogurtsov et al., Org. Lett. 7, 791 (2005)