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Named reactions

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Malayamycin A

Chemical structure of Malayamycin_A
C13H18N4O7
Author Stephen Hanessian
Publication year 2003
Synthesis type Total synthesis
Number of steps 24 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
2,2-Dimethoxypropane, Pyr.TsOH, Na2SO4
94%
Chemical structure + Chemical structure
t-BuLi
75%
Chemical structure
Li(s-Bu)3BH, ZnCl2
CH2Cl2
86%
Chemical structure
DIAD, Ph3P
THF
91%

See the Mitsunobu Reaction
Chemical structure
AcOH
H2O
85%
Chemical structure + Chemical structure
Pyr
89%
Chemical structure
  1. NaH
  2. (4-MeOPh)CH2Br
DMF, THF
84%
Chemical structure
HCl
Dioxane , H2O
88%
Chemical structure
DMSO, (COCl)2, i-Pr2NEt
CH2Cl2

See the Swern Oxidation
Chemical structure
Ph3P+CH3 Br-, TMS2NNa
THF
36% (2 steps)

See the Wittig Reaction
Chemical structure
  1. NaH
  2. AllylBr
DMF
0 °C to RT, 2 h, 93%
Chemical structure
Grubbs catalyst (1st gen.)
CH2Cl2
Reflux, 5.5 h, 89%

See the Olefin Metathesis
Chemical structure
NBS
THF, H2O
RT, 2 h
Chemical structure
NaOH
THF
Reflux, 45 min
Chemical structure
NaN3
2-Methoxyethanol
126 °C, 75 min, 41% (3 steps)
Chemical structure
Dess-Martin Periodinane
CH2Cl2
RT, 3.5 h

See the Dess-Martin Oxidation
Chemical structure
NaBH4
MeOH
0 °C, 10 min
Chemical structure
  1. NaH
  2. MeI
DMF
0 °C to RT, 2 h, 93% (3 steps)

See the Williamson Ether Synthesis
Chemical structure
DDQ
CH2Cl2, H2O
RT, 60 min, 84%
Chemical structure
t-BuCOCl, DMAP
Pyr, Et3N
RT, 36 h
Chemical structure
TMSCl, NaI
MeCN
RT, 16 h, 42% (2 steps)
Chemical structure
Me3P
THF, H2O
RT to Reflux, 35 min

See the Staudinger Reaction
Chemical structure
Cl3CC(O)NCO
CH2Cl2
RT, 30 min
Chemical structure
MeNH2
MeOH, H2O
RT, 52 h, 60% (3 steps)
Chemical structure

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