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Cristatic Acid, Methyl Ester

Chemical structure of Cristatic_Acid_Methyl_Ester
C24H30O5
Author Alois Fürstner
Publication year 2000
Synthesis type Total synthesis
Number of steps 17 (2 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 2
Chemical structure
  1. NaH
  2. PrenylBr
PhMe
35 °C, 19 h, 73%

See the Friedel-Crafts Alkylation
Chemical structure
  1. KH, 18-Crown-6
  2. TMS(CH2)2OCH2Cl
THF
RT, 5 h, 84%
Chemical structure
SeO2, t-BuOOH
CH2Cl2, H2O
RT, 5 h, 61%
Chemical structure
MsCl, LiBr, Et3N
CH2Cl2, THF
0 °C, 3 h, 76%

See the Finkelstein Reaction
Chemical structure

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Part 2 of 2
Chemical structure
+
Chemical structure
t-BuLi
THF
-78 °C, 10 min, 62%

See the Johnson-Corey-Chaykovsky Reaction
Chemical structure
CH2(SO2Ph)2, Pd(PPh3)4, dppe
THF
RT, 14 h, 98%
Chemical structure
3,4-Dihydropyran, Pyr.TsOH
CH2Cl2
0 °C to RT, 4 h, 91%
Chemical structure
n-Bu4N+ F-
THF
50 °C, 16 h, 95%
Chemical structure
MnO2
CH2Cl2
RT, 3 h
Chemical structure
HCl
EtOAc, H2O
RT, 12 h, 87% (2 steps)

See the Paal-Knorr Furan Synthesis
Chemical structure
DDQ
CH2Cl2, H2O
0 °C, 7 h
Chemical structure
MnO2
CH2Cl2
RT, 3 h
Chemical structure
Ph3P=CMe2
THF
0 °C, 14 h, 57% (3 steps)

See the Wittig Reaction
Chemical structure
Al(Hg)
THF, H2O
RT, 3 h
Chemical structure + Chemical structure
n-BuLi
THF, HMPA
-78 to 0 °C, 2 h
Chemical structure
Na(Hg), Na2HPO4
MeOH
0 °C to RT, 5 h, 55% (3 steps)
Chemical structure
n-Bu4N+ F-
HMPA
50 °C, 12 h, 60%
Chemical structure

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