Synthesis of Endiandric Acid A Methyl Ester
C22H24O2
Principal investigator | Kyriacos C. Nicolaou |
---|---|
Publication year | 1982 |
Synthesis type | Total |
Number of steps | 15 (3 parts) |
References |
Part 1 of 3
+
LDA
HMPA, THF
-78 °C, 90%
AcOH
H2O, THF
40 °C, 75%
mCPBA
CH2Cl2
-78 °C, 98%
PhMe
50 °C, 48%
"Also isolated was the Z isomer (48% yield)"
AgNO3,
KCN
EtOH, H2O
RT, 98%
Part 2 of 3
CrO3,
H2SO4
Acetone, H2O
-10 °C
See the Jones Oxidation
"The starting material was synthesized in part 1"
CH2N2
Et2O
0 °C, 75% (2 steps)
18-Crown-6,
KF
DMF
RT, 90%
Part 3 of 3
+
mCPBA
CH2Cl2
-78 °C, 90%
PhMe
50 °C, 39%
"Also isolated was the Z isomer (39% yield)"
H2,
Lindlar Catalyst
CH2Cl2, Quinoline
25 °C