Synthesis of Malayamycin A

Structure of Malayamycin A

C13H18N4O7

Principal investigatorStephen Hanessian
Publication year2003
Synthesis typeTotal
Number of steps 24 (linear)
References
Org. Lett. 2003, 5, 4277.
Part 1 of 1
intermediate structure
Na2SO4, 2,2-Dimethoxypropane, Pyr.TsOH
94%
intermediate structure + intermediate structure
t-BuLi
75%
intermediate structure
ZnCl2, Li(s-Bu)3BH
CH2Cl2
86%
intermediate structure
Ph3P, DIAD
THF
91%
See the Mitsunobu Reaction
intermediate structure
AcOH
H2O
85%
intermediate structure + intermediate structure
Pyr
89%
intermediate structure
  1. NaH
  2. (4-MeOPh)CH2Br
DMF, THF
84%
intermediate structure
HCl
Dioxane , H2O
88%
intermediate structure
(COCl)2, DMSO, i-Pr2NEt
CH2Cl2
See the Swern Oxidation
intermediate structure
TMS2NNa, Ph3P+CH3 Br-
THF
36% (2 steps)
See the Wittig Reaction
intermediate structure
  1. NaH
  2. AllylBr
DMF
0 °C to RT, 2 h, 93%
intermediate structure
Grubbs catalyst (1st gen.)
CH2Cl2
Reflux, 5.5 h, 89%
See the Olefin Metathesis
intermediate structure
NBS
H2O, THF
RT, 2 h
intermediate structure
NaOH
THF
Reflux, 45 min
intermediate structure
NaN3
2-Methoxyethanol
126 °C, 75 min, 41% (3 steps)
intermediate structure
Dess-Martin Periodinane
CH2Cl2
RT, 3.5 h
See the Dess-Martin Oxidation
intermediate structure
NaBH4
MeOH
0 °C, 10 min
intermediate structure
  1. NaH
  2. MeI
DMF
0 °C to RT, 2 h, 93% (3 steps)
See the Williamson Ether Synthesis
intermediate structure
DDQ
CH2Cl2, H2O
RT, 60 min, 84%
intermediate structure
DMAP, t-BuCOCl
Et3N, Pyr
RT, 36 h
intermediate structure
TMSCl, NaI
MeCN
RT, 16 h, 42% (2 steps)
intermediate structure
Me3P
H2O, THF
RT to Reflux, 35 min
See the Staudinger Reaction
intermediate structure
Cl3CC(O)NCO
CH2Cl2
RT, 30 min
intermediate structure
MeNH2
H2O, MeOH
RT, 52 h, 60% (3 steps)
intermediate structure
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