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福山机理题


Fukuyama Group - Group Meeting Problems 10/03/2001

1
EtO2C NH2

1) t-BuOCl, CH2Cl2, –70 °C; O –70 °C; SMe Et3N, –70 to 25 °C 2) Ra-Ni (xs), EtOH, 25 °C

Et

O2C N H Me

2
O2N O HC(NMe2)3 (5 eq) THF, reflux 5h H 80% HN O

H

N CH3

N CH3

3
O OTBS 54% CO2Me MeO2C CHO 1,4-cyclohexadiene PhCl, 150 °C OTBS

4
CHO N PhOH; HBF4 O N

5
F Me N Me Et N CHO POCl3 Me Me Me N F N Et

Fukuyama Group - Group Meeting Problems 10/10/2001
1
N 10% KOH rt, overnight; 4 M HCl rt to 90 °C NO2 N O O

2
1) Bu3SnH, AIBN benzene, ? O Si Br 2) MeLi HO Me3Si

3
N SEM O +

Me N I

1) LDA 2) HCl, PhH rt, 2h CO2Me

3) 4N HCl reflux 4) NaBH4 N H

H

Me N

H OH

4
BnO Me H N O NH2 2) PhMgBr, THF/CH2Cl2, –50 °C; OPMB (MeO)3P, MeOH, 50 °C 83% 1) SOCl2, imidazole, CH2Cl2 –78 °C to rt, 81% BnO Me H N O H

OH

NH

OPMB

H BnO

H BnO

5
N 1) t-BuOCl SnCl4 2) KHMDS H MeO2C OTBDPS N H N

N H H

H CO2Me

OTBDPS

Fukuyama Group - Group Meeting Problems 10/17/2001
1
MeO Me OMe N3 1) TIPSO

O

O MeO Me OMe N H CO2Et OTIPS

OEt t-BuOK, DMF, 105 °C

2) hν, Vycor, CH3CN

2
O TBS TMS +

OLi –80 to –30 °C THF TBSO

O

TMS 84%

3
1. Me2NNH2 2. MeI Ar O Ar = p-NO2C6H4 3. NaH, THF hν, Pyrex 5% CH2=CHCN O2 satd. MeCN N O CN + ArCHO

4
O TBS EtAlCl2 CH2Cl2 rt SMe O SMe TBS 90%

5
O HN O

NO2

HO

Cl

SmI2 (4 eq)

CHCl3 rt

t-BuOK / t-BuOH

Fukuyama Group - Group Meeting Problems 10/24/2001
1
O O NC NC hυ MeCN CN CN O O OH

2

Me EtO2C N H

CO2Et CHO

1)
Ph

N

Me

Me
H

CO2Et CO2Me N H MeN Ph CO2Me

benzene, reflux,1hr 2) DMAD, benzene, rt, 2hr

EtO2C

3
Ph

O N OH

O Ph

AIBN xylene reflux, 35 min 82% N H Ph

4

OAc

1) LDA; TBDMSCl; 66 °C; H3O+ 2) NH4Cl, EDCI, HOBt 3) Cl3COCOCl, TEA MeO 4) CHCl3, aq NaOH, cat. TEBAC 5) H2, PtO2; (Boc)2O, TEA 6) AgBF4, 40 °C

Cl NBoc

MeO O-i-Pr

i-PrO

EDCI; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide TEBAC; triethylbenzylammonium chloride

5
Ar

O N H

CO2Et CO2H Ar =

1) Ac2O, toluene, 50 °C 2) Ar'COCl, pyridine, 60 °C 3) AcOH, 90 °C
Cl

O Ar N H

CO2Et Ar' O

,

Ar' =

O

Fukuyama Group - Group Meeting Problems 10/31/2001
1
BocHN NH2 1) HOCH2SO3Na * H2O, 40 °C 2) RCO2H HOBt, DCC, Et3N
O

R BocHN N

O SO3Na

R=
N

NH O

2
O

H N O OBn O

OEt

1) ArSO2N3 i-Pr2NEt 2) Rh2(OAc)4 CH2Cl2 O

H N O CO2Et

O

3

O Me NH2

Me O

N N H N H 0 °C , in SOCl2

A

N N H

S N N

warmed to r.t.

O

4
O

TMSOTf benzene, CH2Cl2 reflux, 7 hr 98%

Ph

Ph

5
BnO

O

OMe OBn

Cp2ZrCl2, 2 eq n-BuLi BnO BF3?Et2O, THF 65% BnO OBn OH

OBn


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