Synthesis of β-Vetivone More resources available ... - ChemistforChrist

Synthesis of β-Vetivone
O
n-BuSH
Et 2O
H 2SO 4
O
BuS
AcO
AcO
O
H OMe
Base
O
HO
NaBH 4,
MeOH
Ac 2O,
NaOAc, Δ
Na 2CrO 4, AcOH
Ac 2O, 40°C
O
O
O
HO
BuS
HO
BF 3 . Et2O, rt
O
O
O
β−Vetivone
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O
HgCl 2, H 3O +
acetone
MeLi, Et 2O
- 35°C
O
O
O
O
hν, dioxane
, NaH
H OEt
benzene, MeOH
O
O
MeLi, Et 2O
- 35°C
1. Li, NH 3, Et 2O
2. CrO 3
A small amount of the isoprenyl
isomer is also formed:
Other disconnection approaches:
O O
Cl
O
or
HO
O
AcOH, Ac 2O
H 2SO 4
For the - charge there is no easy synthon
O
MnO 2
O