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
J. Am. Chem. Soc. 1982, 104, 5558. J. Am. Chem. Soc. 1982, 104, 5560.
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%
See the Parikh-Doering Oxidation
intermediate structure
Special reagent
LDA
THF
-78 °C to RT, 78%
See the Horner-Wadsworth-Emmons Reaction
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
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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
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Part 3 of 3
intermediate structure + intermediate structure
Pyr, Cu(OAc)2
MeOH
RT, 70%
See the Eglinton Reaction
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)
See the Diels-Alder Reaction
intermediate structure
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