Synthesis of Laurenene

Structure of Laurenene

C20H32

Principal investigatorMichael T. Crimmins
Publication year1987
Synthesis typeTotal
Number of steps 27 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure + intermediate structure
HMPA, (n-Bu3PCuI)4
THF
-50 °C to RT, 3 h, 60%
intermediate structure
HCl
Acetone, H2O
RT, 6 h
intermediate structure
NaOMe
MeOH
0 °C, 30 min
intermediate structure
Me2CuLi
Et2O
-78 °C, 30 min
intermediate structure
LiCl
DMSO, H2O
140 °C, 15 min, 71% (4 steps)
intermediate structure
(CH2OH)2, TsOH
PhH
80 °C, 5 h
intermediate structure
n-Bu4N+ F-, KF
MeCN
80 °C, 2 h
intermediate structure
n-BuLi, CO2
THF
-78 °C
intermediate structure
CH2N2
Et2O
90 & (4 steps)
intermediate structure
Me2CuLi
Et2O
-78 °C, 30 min
intermediate structure
HCl
Acetone, H2O
RT, 6 h, 89% (2 steps)
intermediate structure
n-Bu4N+ F-, TMSCH2CO2Et
THF
-78 °C to RT, 2 h
intermediate structure
Pd(OAc)2, 1,4-Benzoquinone
MeCN
RT, 6 h, 80% (2 steps)
"The yield was 89 % brsm."
intermediate structure
PhCl
110 °C, , 87%
intermediate structure
LiAlH4
Et2O
RT
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C
See the Swern Oxidation
intermediate structure + intermediate structure
CH2Cl2
40 °C, 60 min, 89 % (3 steps)
See the Wittig Reaction
intermediate structure
Na
Et2O, NH3
-33 °C, 5 min
intermediate structure
H2, Pd/C
EtOH
80% (2 steps)
intermediate structure
LiAlH4
Et2O
RT
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C
intermediate structure
TsOH
PhH
80 °C, , 75% (3 steps)
intermediate structure
NaBH4, CeCl3
MeOH
23%
See the Luche Reduction
"Also isolated was the C13-epimer (67 % yield)."
intermediate structure
KH, n-Bu3SnCH2I
THF
intermediate structure
n-BuLi
Hexane(s)
0 °C, , 57% (2 steps)
intermediate structure
TsCl
Pyr
intermediate structure
LiBHEt3
THF
72% (2 steps)
intermediate structure