Synthesis of Retigeranic Acid
C25H38O2
| Principal investigator | Paul A. Wender |
|---|---|
| Publication year | 1990 |
| Synthesis type | Total |
| Number of steps | 23 (3 parts) |
| References |
Part 1 of 3
+
Pig liver esterase
Buffer (pH = 7)
20 °C, 94%
"Cristallized to >99 % ee."
Ph3P,
2,2?-Dipyridyl disulfide
CH2Cl2
RT, 36 h, 96%
+
CuI,
Li
Et2O
-78 to 0 °C, 5 h, 90%
LiAlH4
Et2O
HClO4,
Pd/C,
H2
1 atm
EtOH
RT, 15 h, 93% (2 steps)
hν
Cyclohexane
7 h, 24%
"Also isolate was a regioisomer (48 % yield) which was photoisomerized to the desired product."
HCONH2
hν
Acetone, t-BuOH
7 h
"Yield not reported."
MeI,
KOH
DMSO
RT, 48 h, 54%
"The yield was 80 % at 67 % conversion."
SeO2,
t-BuOOH
DCE
Reflux, 23 h, 53%
Part 2 of 3
H2,
(Ph3P)3RhCl
1 atm
PhH
RT, 3.5 h, 90-94%
Br2
AcOH
Part 3 of 3
+
+
+
CH(OMe)2NMe2
AcOH
Reflux, 2 h, 65% (2 steps)
KOt-Bu
DMSO
100 °C
Pd/C,
H2
27 atm
PhH
RT, 14 d, 25%
"Also isolated was the C2-epimer (28 % yield) and internal alkenes (43 % yield) which were recycled."
LiAlH4
THF
-5 °C to RT, 14 h
"Yield not reported."
+
HCrO3Cl.Pyr
CH2Cl2
RT, 4 h
"Yield not reported."