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



