Synthesis of Laurenene
C20H32
Principal investigator | Michael T. Crimmins |
---|---|
Publication year | 1987 |
Synthesis type | Total |
Number of steps | 27 (linear) |
References |
Part 1 of 1
+
+
+
HCl
Acetone, H2O
RT, 6 h
(CH2OH)2,
TsOH
PhH
80 °C, 5 h
n-Bu4N+ F-,
KF
MeCN
80 °C, 2 h
n-BuLi,
CO2
THF
-78 °C
CH2N2
Et2O
90 & (4 steps)
HCl
Acetone, H2O
RT, 6 h, 89% (2 steps)
n-Bu4N+ F-,
TMSCH2CO2Et
THF
-78 °C to RT, 2 h
1,4-Benzoquinone,
Pd(OAc)2
MeCN
RT, 6 h, 80% (2 steps)
See the Saegusa-Ito Oxidation
"The yield was 89 % brsm."
hν
PhCl
110 °C, 87%
LiAlH4
Et2O
RT
Na
Et2O, NH3
-33 °C, 5 min
H2,
Pd/C
EtOH
80% (2 steps)
LiAlH4
Et2O
RT
(COCl)2,
DMSO,
Et3N
CH2Cl2
-78 °C
KH,
n-Bu3SnCH2I
THF
TsCl
Pyr
LiBHEt3
THF
72% (2 steps)