Synthesis of Martinellic Acid

Structure of Martinellic Acid

C27H41N7O2

Principal investigatorBarry B. Snider
Publication year2001
Synthesis typeTotal
Number of steps 15 (linear)
References
Org. Lett. 2001, 3, 4217.
Part 1 of 1
intermediate structure
LiAlH4
THF
-78 °C to RT, 5 h, 81%
intermediate structure + intermediate structure
PhMe
Reflux, 24 h, 82%
intermediate structure
MnO2
CH2Cl2
RT, 12 h, 87%
intermediate structure
N-Benzylglycine
Dean-Stark
PhMe
Reflux, 15 h, 57%
See the Huisgen Cycloaddition
"Also isolated was the C2-epimer (3 % yield)."
intermediate structure
LiBH4
MeOH, THF
Reflux, 8 d, 91%
intermediate structure
AcCl, Et3N
CH2Cl2
0 °C to RT, 3 h, 79%
intermediate structure
CO, NaOAc, Pd(OAc)2, Ph3P
4 atm
MeOH
120 °C, 96 h, 72%
intermediate structure
(CF3CO)2O, Pyr
CH2Cl2
0 °C to RT, 12.5 h, 74%
intermediate structure
Pyr, MsCl
CH2Cl2
0 °C to RT, 24 h
intermediate structure
NaN3
DMF
RT, 36 h, 54% (2 steps)
intermediate structure
NaOMe
CH2Cl2, MeOH
RT, 60 min, 82%
intermediate structure
H2, HCl, Pd(OH)2/C
1 atm
H2O, MeOH
RT, 3 h, 84%
intermediate structure
NaHCO3, BrCN
MeOH
0 °C, 60 min, 100%
intermediate structure
PrenylNH2
HFIPA
120 °C, 32 h
intermediate structure
NaOH
H2O, MeOH
Reflux, 14 h, 62% (2 steps)
intermediate structure
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