Synthesis of Endiandric Acid A Methyl Ester

Structure of Endiandric Acid A Methyl Ester

C22H24O2

Principal investigatorKyriacos C. Nicolaou
Publication year1982
Synthesis typeTotal
Number of steps 15 (3 parts)
References
Part 1 of 3
intermediate structure + intermediate structure
LDA
HMPA, THF
-78 °C, 90%
intermediate structure
AcOH
H2O, THF
40 °C, 75%
intermediate structure
Et3N, Pyr.SO3
DMSO
RT, 80%
intermediate structure
Special reagent
LDA
THF
-78 °C to RT, 78%
intermediate structure
mCPBA
CH2Cl2
-78 °C, 98%
intermediate structure
PhMe
50 °C, 48%
"Also isolated was the Z isomer (48% yield)"
intermediate structure
AgNO3, KCN
EtOH, H2O
RT, 98%
intermediate structure
Part 2 of 3
intermediate structure
CrO3, H2SO4
Acetone, H2O
-10 °C
See the Jones Oxidation
"The starting material was synthesized in part 1"
intermediate structure
CH2N2
Et2O
0 °C, 75% (2 steps)
intermediate structure
18-Crown-6, KF
DMF
RT, 90%
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
Pyr, Cu(OAc)2
MeOH
RT, 70%
intermediate structure
mCPBA
CH2Cl2
-78 °C, 90%
intermediate structure
PhMe
50 °C, 39%
"Also isolated was the Z isomer (39% yield)"
intermediate structure
H2, Lindlar Catalyst
CH2Cl2, Quinoline
25 °C
intermediate structure
PhMe
100 °C, 30% (2 steps)
intermediate structure