Synthesis of Retigeranic Acid
C25H38O2
Principal investigator | Elias J. Corey |
---|---|
Publication year | 1985 |
Synthesis type | Total |
Number of steps | 27 (linear) |
References |
Part 1 of 1
+
+
LiAlH4
Et2O
-20 °C, 90 min, 99%
KOH
MeOH
RT, 15 h, 89% (2 steps)
H2
65 atm
THF
RT, 6.5 h
KHSO4
40 mmHg
150 °C, 82%
LiAlH4
Et2O
0 °C, 30 min, 99%
n-Bu3P,
o-NO2PhSeCN
THF
RT, 60 min
H2SO4
H2O, MeOH
RT, 100%
(COCl)2
PhH
RT, 2 h
Et3N
PhH
RT, 5 min, 80% (2 steps)
Et3N,
CuOTf
PhH
RT, 10 min
NaIO4
Dioxane , H2O
RT, 12 h
Al(Hg)
H2O, THF
0 °C to RT, 3 h, 65% (3 steps)
H2,
Pd/C
1 atm
Pyr, THF
RT, 24 h, 83%
NaOMe
MeOH
-78 °C, 89%
TsN3
EtOH
RT, 12 h
Catecholborane,
n-Bu4N+ OAc-
CHCl3
RT to 65 °C, 90 min, 83% (2 steps)
OsO4
Pyr
RT, 60 min