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
Part 1 of 2
intermediate structure
  1. NaH
  2. PrenylBr
PhMe
35 °C, 19 h, 73%
intermediate structure
  1. KH
  2. 18-Crown-6
  3. TMS(CH2)2OCH2Cl
THF
RT, 5 h, 84%
intermediate structure
SeO2, t-BuOOH
CH2Cl2, H2O
RT, 5 h, 61%
intermediate structure
Et3N, MsCl, LiBr
CH2Cl2, THF
0 °C, 3 h, 76%
intermediate structure
Part 2 of 2
intermediate structure + intermediate structure
t-BuLi
THF
-78 °C, 10 min, 62%
intermediate structure
Pd(PPh3)4, CH2(SO2Ph)2, dppe
THF
RT, 14 h, 98%
intermediate structure
3,4-Dihydropyran, Pyr.TsOH
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)
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
Na(Hg), Na2HPO4
MeOH
0 °C to RT, 5 h, 55% (3 steps)
intermediate structure
n-Bu4N+ F-
HMPA
50 °C, 12 h, 60%
intermediate structure