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Named reactions

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Search synthesis

Laurenene

Chemical structure of Laurenene
C20H32
Author Michael T. Crimmins
Publication year 1987
Synthesis type Total synthesis
Number of steps 27 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
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Chemical structure
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Chemical structure
(n-Bu3PCuI)4, HMPA
THF
-50 °C to RT, 3 h, 60%

See the Michael Addition
Chemical structure
HCl
Acetone, H2O
RT, 6 h
Chemical structure
NaOMe
MeOH
0 °C, 30 min

See the Knoevenagel Condensation
Chemical structure
Me2CuLi
Et2O
-78 °C, 30 min

See the Michael Addition
Chemical structure
LiCl
DMSO, H2O
140 °C, 15 min, 71% (4 steps)

See the Krapcho Decarboxylation
Chemical structure
(CH2OH)2, TsOH
PhH
80 °C, 5 h
Chemical structure
n-Bu4N+ F-, KF
MeCN
80 °C, 2 h
Chemical structure
n-BuLi, CO2
THF
-78 °C
Chemical structure
CH2N2
Et2O
90 & (4 steps)
Chemical structure
Me2CuLi
Et2O
-78 °C, 30 min

See the Michael Addition
Chemical structure
HCl
Acetone, H2O
RT, 6 h, 89% (2 steps)

Selectivity : 66:33 Z/E
Chemical structure
TMSCH2CO2Et, n-Bu4N+ F-
THF
-78 °C to RT, 2 h
Chemical structure
Pd(OAc)2, 1,4-Benzoquinone
MeCN
RT, 6 h, 80% (2 steps)

See the Saegusa-Ito Oxidation
The yield was 89 % brsm.
Chemical structure
PhCl
110 °C, 87%

Selectivity : 60:40 R/S
Chemical structure
LiAlH4
Et2O
RT
Chemical structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C

See the Swern Oxidation
Chemical structure + Chemical structure
CH2Cl2
40 °C, 60 min, 89 % (3 steps)

See the Wittig Reaction
Chemical structure
Na
NH3, Et2O
-33 °C, 5 min
Chemical structure
H2, Pd/C
EtOH
80% (2 steps)
Chemical structure
LiAlH4
Et2O
RT
Chemical structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C
Chemical structure
TsOH
PhH
80 °C, 75% (3 steps)

See the Claisen-Schmidt Condensation
Chemical structure
NaBH4, CeCl3
MeOH
23%

See the Luche Reduction
Also isolated was the C13-epimer (67 % yield).
Chemical structure
KH, n-Bu3SnCH2I
THF
Chemical structure
n-BuLi
Hexane(s)
0 °C, 57% (2 steps)

See the Wittig Rearrangement-[2,3]
Chemical structure
TsCl
Pyr
Chemical structure
LiBHEt3
THF
72% (2 steps)
Chemical structure

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