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Named reactions

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Asteltoxin

"Dedicated to the memory of Professor Kunio Sakan."

Chemical structure of Asteltoxin
C23H30O7
Author Stuart L. Schreiber
Publication year 1984
Synthesis type Total synthesis
Number of steps 20 (3 parts)
References

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
+
Chemical structure
PhH
RT, 6 h, 63%

See the Paterno-Büchi Reaction
Chemical structure
mCPBA, NaHCO3
CH2Cl2
80%

See the Prilezhaev Reaction
Chemical structure
HCl
THF, H2O
Chemical structure
Me2NNH2, MgSO4
CH2Cl2
72% (2 steps)
Chemical structure
EtMgBr
THF
RT, 48 h

See the Grignard Reaction
Chemical structure
CuSO4, Camphorsulfonic acid
Acetone
55% (2 steps)
Chemical structure
Li
NH3, Et2O
98%

See the Birch Reduction
Chemical structure
o-NO2PhSeCN, n-Bu3P
THF
Chemical structure
H2O2
THF, H2O
81% (2 steps)

See the Grieco Dehydration
Chemical structure
  1. O3, NaHCO3
  2. Me2S
CH2Cl2, MeOH
-78 °C to RT
Chemical structure + Chemical structure
n-BuLi
THF
-78 °C, 40 min, 67% (2 steps)

Also isolated was the C1-epimer (21 % yield).
Chemical structure
Camphorsulfonic acid
CH2Cl2
RT, 8 h
Chemical structure
(CF3CO)2O, NaOAc, 2,6-Lutidine
Ac2O
RT, 60 min

See the Pummerer Rearrangement
Chemical structure
HgCl2, CaCO3
MeCN, H2O
RT, 2 h, 60% (2 steps)
Chemical structure

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Part 2 of 3
Chemical structure
MeI, K2CO3
Acetone
Chemical structure
NaNH2, CO2
Et2O, NH3
Chemical structure
CDI
THF
Chemical structure
Me2SO4, K2CO3
Acetone
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
i-Pr2NLi, HMPA
THF
-78 °C, 20 min, 80%

See the Aldol Addition
Chemical structure
TsCl, Et3N, DMAP
CH2Cl2
RT, 12 h, 82%
Chemical structure

Report an error in this part

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