Synthesis of Retigeranic Acid

Structure of Retigeranic Acid

C25H38O2

Principal investigatorElias J. Corey
Publication year1985
Synthesis typeTotal
Number of steps 27 (linear)
References
Part 1 of 1
intermediate structure
LiAlH4
Et2O
-20 °C, 90 min, 99%
intermediate structure
DEAD, Ph3P, BzOH
Et2O
-25 °C, 60 min
intermediate structure
KOH
MeOH
RT, 15 h, 89% (2 steps)
intermediate structure
H2
THF
RT, 6.5 h
intermediate structure
CrO3, H2SO4
Acetone, H2O
93% (2 steps)
See the Jones Oxidation
intermediate structure
VinylMgBr
Et2O
0 °C, , 97%
intermediate structure
KHSO4
150 °C, , 82%
intermediate structure + intermediate structure
98-105 °C, 120 h, 61%
intermediate structure + intermediate structure
TMS2NK
PhMe
RT, 12 h, 80%
See the Wittig Reaction
intermediate structure
LiAlH4
Et2O
0 °C, 30 min, 99%
intermediate structure
n-Bu3P, o-NO2PhSeCN
THF
RT, 60 min
intermediate structure
Me2S, mCPBA
CH2Cl2
-78 °C to RT, 15 h, 75% (2 steps)
intermediate structure
H2SO4
H2O, MeOH
RT, , 100%
intermediate structure
(COCl)2
PhH
RT, 2 h
intermediate structure
Et3N
PhH
RT, 5 min, 80% (2 steps)
intermediate structure
n-BuLi, MeCH(SMe)2
THF
-78 °C, , 73%
intermediate structure
Et3N, CuOTf
PhH
RT, 10 min
intermediate structure
NaIO4
Dioxane , H2O
RT, 12 h
intermediate structure
Al(Hg)
H2O, THF
0 °C to RT, 3 h, 65% (3 steps)
intermediate structure
H2, Pd/C
Pyr, THF
RT, 24 h, 83%
intermediate structure
NaOMe
MeOH
-78 °C, , 89%
intermediate structure
TsN3
EtOH
RT, 12 h
intermediate structure
Catecholborane, n-Bu4N+ OAc-
CHCl3
RT to 65 °C, 90 min, 83% (2 steps)
intermediate structure
OsO4
Pyr
RT, 60 min
intermediate structure
Pb(OAc)4
CH2Cl2
-78 to 0 °C, 30 min, 69% (2 steps)
intermediate structure
Al2O3
CH2Cl2
RT, 2 h, 70%
intermediate structure
NaH2PO4, NaClO2, 2-Methyl-2-butene
H2O, t-BuOH
RT, 30 min, 85%
intermediate structure