Synthesis of Cristatic Acid, Methyl Ester

C24H30O5
Principal investigator | Alois Fürstner |
---|---|
Publication year | 2000 |
Synthesis type | Total |
Number of steps | 17 (2 parts) |
References |
Part 1 of 2


- 18-Crown-6 , KH
- TMS(CH2)2OCH2Cl
THF
RT, 5 h, 84%

t-BuOOH,
SeO2
CH2Cl2, H2O
RT, 5 h, 61%


Part 2 of 2
+
+



dppe,
CH2(SO2Ph)2,
Pd(PPh3)4
THF
RT, 14 h, 98%

Pyr.TsOH,
3,4-Dihydropyran
CH2Cl2
0 °C to RT, 4 h, 91%

n-Bu4N+ F-
THF
50 °C, 16 h, 95%

MnO2
CH2Cl2
RT, 3 h


DDQ
CH2Cl2, H2O
0 °C, 7 h

MnO2
CH2Cl2
RT, 3 h


Al(Hg)
H2O, THF
RT, 3 h


n-BuLi
HMPA, THF
-78 to 0 °C, 2 h

Na2HPO4,
Na(Hg)
MeOH
0 °C to RT, 5 h, 55% (3 steps)

n-Bu4N+ F-
HMPA
50 °C, 12 h, 60%
