Synthesis of Martinellic Acid

C27H41N7O2
Principal investigator | Barry B. Snider |
---|---|
Publication year | 2001 |
Synthesis type | Total |
Number of steps | 15 (linear) |
References |
Part 1 of 1
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LiAlH4
THF
-78 °C to RT, 5 h, 81%


PhMe
Reflux, 24 h, 82%

MnO2
CH2Cl2
RT, 12 h, 87%

N-Benzylglycine
Dean-Stark
PhMe
Reflux, 15 h, 57%
See the Huisgen Cycloaddition
"Also isolated was the C2-epimer (3 % yield)."

LiBH4
MeOH, THF
Reflux, 8 d, 91%

AcCl,
Et3N
CH2Cl2
0 °C to RT, 3 h, 79%

CO,
NaOAc,
Pd(OAc)2,
Ph3P
4 atm
MeOH
120 °C, 96 h, 72%

(CF3CO)2O,
Pyr
CH2Cl2
0 °C to RT, 12.5 h, 74%

Pyr,
MsCl
CH2Cl2
0 °C to RT, 24 h

NaN3
DMF
RT, 36 h, 54% (2 steps)

NaOMe
CH2Cl2, MeOH
RT, 60 min, 82%

H2,
HCl,
Pd(OH)2/C
1 atm
H2O, MeOH
RT, 3 h, 84%

NaHCO3,
BrCN
MeOH
0 °C, 60 min, 100%

PrenylNH2
HFIPA
120 °C, 32 h

NaOH
H2O, MeOH
Reflux, 14 h, 62% (2 steps)
