Synthesis of Cristatic Acid, Methyl Ester

Structure of Cristatic Acid, Methyl Ester

C24H30O5

Principal investigatorAlois Fürstner
Publication year2000
Synthesis typeTotal
Number of steps 17 (2 parts)
References
Org. Lett. 2000, 2, 2467.
Part 1 of 2
intermediate structure
  1. NaH
  2. PrenylBr
PhMe
35 °C, 19 h, 73%
See the Friedel-Crafts Alkylation
intermediate structure
  1. 18-Crown-6 , KH
  2. TMS(CH2)2OCH2Cl
THF
RT, 5 h, 84%
intermediate structure
t-BuOOH, SeO2
CH2Cl2, H2O
RT, 5 h, 61%
intermediate structure
LiBr, MsCl, Et3N
CH2Cl2, THF
0 °C, 3 h, 76%
See the Finkelstein Reaction
intermediate structure
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Part 2 of 2
intermediate structure + intermediate structure
t-BuLi
THF
-78 °C, 10 min, 62%
See the Johnson-Corey-Chaykovsky Reaction
intermediate structure
dppe, CH2(SO2Ph)2, Pd(PPh3)4
THF
RT, 14 h, 98%
intermediate structure
Pyr.TsOH, 3,4-Dihydropyran
CH2Cl2
0 °C to RT, 4 h, 91%
intermediate structure
n-Bu4N+ F-
THF
50 °C, 16 h, 95%
intermediate structure
MnO2
CH2Cl2
RT, 3 h
intermediate structure
HCl
EtOAc, H2O
RT, 12 h, 87% (2 steps)
See the Paal-Knorr Furan Synthesis
intermediate structure
DDQ
CH2Cl2, H2O
0 °C, 7 h
intermediate structure
MnO2
CH2Cl2
RT, 3 h
intermediate structure
Ph3P=CMe2
THF
0 °C, 14 h, 57% (3 steps)
See the Wittig Reaction
intermediate structure
Al(Hg)
H2O, THF
RT, 3 h
intermediate structure + intermediate structure
n-BuLi
HMPA, THF
-78 to 0 °C, 2 h
intermediate structure
Na2HPO4, Na(Hg)
MeOH
0 °C to RT, 5 h, 55% (3 steps)
intermediate structure
n-Bu4N+ F-
HMPA
50 °C, 12 h, 60%
intermediate structure
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