# 福山机理题

Fukuyama Group - Group Meeting Problems 09/05/2001

1
1) NaCN, DMSO, 130 °C OAc CO2Me OBn 2) 0.5 mol% [Rh(CO)2Cl]2 toluene, 110 °C, 30 min 93%

H BnO

2

/>Br Br N Ph t-BuLi (5.5 eq), Et2O, –78 °C; TMEDA, –78 °C to rt; PhCOCOPh N Ph OH Ph Ph OH

3
LTA (1.5 eq) CO (105 atm) OH benzene, 80 °C 63% O O

4

O

O Cu powder PhH reflux 3.5 h O N2 1N HCl THF 65 °C 1h

O +

O

O 9 t-BuLi (4 eq) THF –78 °C A : 1

O

5

n-Bu

CO2Et

Br Br

O CO2Et

1) A THF, –78 °C 2) H (silica gel) benzene, reflux
+

n-Bu CO2Et H

Fukuyama Group - Group Meeting Problems 09/12/2001
O

1
O O ·
F3C CF3 F3C OH TFE

n-BuLi THF, –78 °C, 20 min; then
O N O

HO

OH HFIP

–78 °C to –30 °C, 1 hr; then HCl / HFIP-TFE –78 °C to rt

78% (86%ee)

2
H O H Cl Cl

CH2N2, Et2O 0 °C, 2 h; evap; cyclopentadiene (10 eq*) Et3N (3 eq*) TFE /Et2O (1 : 1) –78 °C to rt TFE = trifluoroethanol C13H13ClO 74%

1) LAH, Et2O, 0 °C 2) KH (5 eq*), THF 0 °C to rt

H H

H CHO

(two isomer 10.4 : 1) *

?? Rκ?aR?a
O O

76% (2 steps)

3
OH CF3CO3H (8eq*) + O

*

?? Rκ?aR!?a

CF3CO2H, CH2Cl2

OH

4
MeO2C MeO2C OH O Bu 1. propargyl alcohol PhI(OAc)2, CH3CN 2. Ph3SnH, Et3B toluene 3. 1 M HCl, Et2O CO2Me MeO2C Bu O OH O

5
R N H Bn CO2Me HN CHO N

Bn

benzoic acid, benzene reflux, 10 hr

N H 79%

R CO2Me

R=

Fukuyama Group - Group Meeting Problems 09/19/2001

1

P N H

1) COCl2, DMAP, DMF 25 °C, 1 hr 2) NH2CH2CH2NH2, DMAP CH2Cl2, 25 °C, 1 hr 3) hν (lamp equipped with pyrex filter) THF HN

O NH

P N H

NO2

NO2

2
Br OCH3 tert-BuLi;

i-PrO

O

;
i-PrO O

i-PrO HO i-PrO H O CH3

Li CH3

; aq NH4Cl

3

CO2Me 1) SnCl4, toluene, –78 °C; NaHCO3, toluene, 80 °C NO2 Me 2) H2, RaneyNi, MeOH 160 psi, rt HO H

OH H Me H NH O

4
O CO2Et 1) acetone, Ac2O ZnCl2, 48% 2) PPh3Br n-BuLi, Et2O 85% C12H18O2 1) DIBAL, CH2Cl2 72% 2) (COCl)2, DMSO Et3N, THF, 68% 3) DBU, CH2Cl2 89% CHO

5

OH 1) PhI(OAc)2 CF3CH2OH H CO2H 2) NaHCO3, MeOH 0 °C to rt 54% (2 steps) 3) MeMgBr, CuI (cat.) 60% 4) PhI(OAc)2, I2 CH2Cl2, 80 % O O CO2Me N H AcO Cbz

NHCbz

Fukuyama Group - Group Meeting Problems 09/26/2001

1

O O MeO N3 CHO

CO2Me

1) PPh3, THF; NaBH4, MeOH, rt 2) I2, CH2Cl2, Et2O, rt

O O MeO N

H H O

O

2

OAc C CCH2OTBS O NMe N I AgOTf CH3CN, 70 °C; BnMe3NCN rt

OAc

OTBS

N O 40%

NMe

3

NH2 N3

p-Cl-C6H4CHO cat. AcOH EtOH , reflux

1) PMe3 , Toluene , rt; Ph2C=C=O 2) Pd/C , Toluene, reflux

p-Cl-C6H4 N N Ph

CH3

4
O CH3 H 3C

HO CH 3 1) Eu(fod)3 (10 mol%), toluene, 80 °C, 36 h, 84% 2) hν, Corex, 19 h, 79% 3) LiDBB, THF, –78 °C to 10 °C, 35 h, 57% LiDBB; lithium di-tert-butylbiphenylide H3C H 3C H CH3

5
1) MCPBA N 2) (CF3CO)2O; aq. Na2CO3 N OH

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