Synthesis of Malayamycin A

C13H18N4O7
Principal investigator | Stephen Hanessian |
---|---|
Publication year | 2003 |
Synthesis type | Total |
Number of steps | 24 (linear) |
References |
Part 1 of 1
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Na2SO4,
2,2-Dimethoxypropane,
Pyr.TsOH
94%


t-BuLi
75%

ZnCl2,
Li(s-Bu)3BH
CH2Cl2
86%


AcOH
H2O
85%


Pyr
89%

- NaH
- (4-MeOPh)CH2Br
DMF, THF
84%

HCl
Dioxane , H2O
88%



- NaH
- AllylBr
DMF
0 °C to RT, 2 h, 93%


NBS
H2O, THF
RT, 2 h

NaOH
THF
Reflux, 45 min

NaN3
2-Methoxyethanol
126 °C, 75 min, 41% (3 steps)


NaBH4
MeOH
0 °C, 10 min


DDQ
CH2Cl2, H2O
RT, 60 min, 84%

DMAP,
t-BuCOCl
Et3N, Pyr
RT, 36 h

TMSCl,
NaI
MeCN
RT, 16 h, 42% (2 steps)


Cl3CC(O)NCO
CH2Cl2
RT, 30 min

MeNH2
H2O, MeOH
RT, 52 h, 60% (3 steps)
