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Named reactions

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Aspidophytine

"This article is dedicated to the memory of Jason D. Altom (October 6, 1971-August 15, 1998)."

Chemical structure of Aspidophytine
C22H26N2O4
Author Elias J. Corey
Publication year 1999
Synthesis type Total synthesis
Number of steps 20 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
Fe, SiO2
PhMe, AcOH
Reflux, 20 min, 71 %

See the Leimgruber-Batcho Indole Synthesis
Chemical structure
MeI, KOH, n-Bu4N+ I-
THF
RT, 3 h, 94 %
Chemical structure
POCl3
DMF
0 to 35 °C, 60 min, 99 %

See the Vilsmeier-Haack Formylation
Chemical structure
NH4OAc
MeNO2
Reflux, 60 min, 92 %

See the Henry Reaction
Chemical structure
LiAlH4
THF
0 °C to Reflux, 60 min, 88 %
Chemical structure

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Part 2 of 3
Chemical structure
+
Chemical structure
CeCl3
THF
0 °C, 82 %

See the Michael Addition
Chemical structure
CBS Reagent, Catecholborane
CH2Cl2
-78 °C, 10 h, 94 %

Selectivity : 99:01 er
See the Corey-Itsuno Reaction
Chemical structure
Na(Hg)
MeOH
RT, 2 h, 82 %
Chemical structure
Ac2O, DMAP
CH2Cl2, Et3N
RT, 60 min, 97 %
Chemical structure
  1. i-Pr2NLi
  2. TBSCl
THF
-78 °C to Reflux, 4.5 h

See the Ireland-Claisen Rearrangement
Chemical structure
EDC, DMAP
i-PrOH
40 °C, 3 h, 57 % (2 steps)
Chemical structure
OsO4, NMO
Acetone, H2O
RT, 6 h, 57 %

See the Upjohn Dihydroxylation
Chemical structure
NaIO4
THF, H2O
RT, 35 min, 98 %
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
(CF3CO)2O, NaBH3CN
MeCN
0 °C to RT, 2.5 h, 66 %

See the Hosomi-Sakurai Reaction
Chemical structure
NaOH
EtOH
75 °C, 20 h, 88 %
Chemical structure
K3Fe(CN)6, NaHCO3
t-BuOH, H2O
RT, 5 min, 92 %
Chemical structure
OsO4, DMAP
t-BuOH, H2O
Chemical structure
Pb(OAc)4
AcOH, CH2Cl2
-20 °C, 10 min, 71 % (2 steps)

See the Criegee Reaction
Chemical structure
  1. TMS2NK
  2. PhNTf2
THF
-78 °C, 30 min, 54 %
Chemical structure
Pd(PPh3)4, n-Bu3SnH
THF
RT, 60 min, 86 %

See the Stille Coupling
Chemical structure

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