Bài 1:

1. H2, PtO2, EtOH 1. NaOMe, MeOH, heat

2. CCl3COCl, Zn, Et2O, 2. DIBAL-H O
ultrasound 3. Me3SiI
A

Me
Name?
1. KH, 18-crown-6 HO
2. LiAlH4
HO
B Me
Name reaction?
Me Me
B(pin)
HO O
1.
2. 1. LDA, A
Me 2. DBU, 40°C
Me

Me Name reactions? Me
CO2Me
B(pin) A= OMe
MeO2C

1) DBU, 100°C Me 1. Burgess reagent

Me
2) o-DCB, mW, 1. 1O2, 0 °C
200 °C O 2. DIBAL-H
2. H2, Pd/C, MeOH
C 3. 1O2, then PMe3
Name reaction? OMe O
Me H
Me OH OH
(–)-Vinigrol

Bài 2:
 Highly Efficient Total Synthesis of the Marine Natural Products
(+)-Avarone, (+)-Avarol, (-)-Neoavarone, (-)-Neoavarol and (+)-Aureol
J. Sakurai, T. Oguchi, K. Watanabe, H. Abe, S. Kanno, M. Ishikawa, and T. Katoh
Chem. Eur. J. 2008, 14, 829 – 837

i.
ii.
Me
MeO H2 (1 atm),
O 1. Ph3P+CH3Br-, tBuOK, 10% Pd/C,
Me
H benzene, reflux NEt3/MeOH 50:1 +
O
O
Me 2. 4 M HCl, THF, rt
O
O
Me
Name of familiar compound? O
Synthesis? 80% 13%

MeO
Me
H
Me

Me
X

OH

structure?
HO HO BF3 Et2O,
Me Me
H O2, salcomine, H CH2Cl2,
Me Me -50 °C -> -5 °C
DMF, rt

Me Me

(-)-neoavarone (-)-neoavarol

MeO
Me
H
Me

Me

X (+)-aureol
OH

HO
Me BF3 Et2O,
RhCl3 3 H2O, 2. O2, salcomine, H CH2Cl2,
EtOH, reflux Me -50 °C -> -5 °C
DMF, rt

Me
Me
(+)-avarone (+)-avarol