Synthesis of Laurenene

Structure of Laurenene

C20H32

Principal investigatorLeo A. Paquette
Publication year1988
Synthesis typeFormal
Number of steps 20 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
CuBr.Me2S
THF, Me2S
-78 to 0 °C, 6 h
intermediate structure
HCl
Acetone, H2O
RT, 3 d, 79% (2 steps)
See the Aldol Addition
intermediate structure
MsCl, Et3N
CH2Cl2
0 °C, 30 min
intermediate structure
DBU
CH2Cl2
RT, ON, 76% (2 steps)
intermediate structure
MeLi
Et2O
-78 °C to RT, ON
intermediate structure
HCrO3Cl.Pyr, Celite
CH2Cl2
RT, ON, 70% (2 steps)
intermediate structure + intermediate structure
CuBr.Me2S
THF, Me2S
-78 to 0 °C, , 68%
intermediate structure
HCl
THF, H2O
RT, , 71%
See the Aldol Addition
intermediate structure
ClC(S)O(p-MePh), Pyr
THF
RT, ON, 84%
intermediate structure
200 °C, , 100%
intermediate structure
TMSCN, ZnI2
PhH
RT, 18 h, 96%
intermediate structure
POCl3, DBU
Pyr
Reflux, 20 h, 92%
intermediate structure
Mg
MeOH
RT, 11 h, 95%
intermediate structure + intermediate structure
i-Pr2NLi, HMPA
THF
-78 °C to RT, 6 h, 83%
intermediate structure
i-Bu2AlH
PhH
RT, 60 min
intermediate structure
NH2NH2, K2CO3
Diethylene glycol
260 °C, 19 h, 63% (2 steps)
intermediate structure
  1. BH3.Me2S
  2. H2O2
  3. H2O
THF
0 to 50 °C, 43 h
intermediate structure + intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 22 min, 62% (2 steps)
See the Swern Oxidation
"Also isolated was the C4-ketone (10 % yield)."
intermediate structure
TsOH
PhH
Reflux, 4 h, 78%
intermediate structure
Remaining...
9% (5 steps)
"See : J. Am. Chem. Soc. 1987, 109, 6199."
intermediate structure