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Named reactions

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Ginkgolide B

Chemical structure of Ginkgolide_B
C20H24O10
Author Elias J. Corey
Publication year 1988
Synthesis type Total synthesis
Number of steps 26 (2 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 2
Chemical structure
+
Chemical structure
(COCl)2
PhH
RT, 85%
Chemical structure
BF3.OEt2
CH2Cl2
-20 °C, 92%
Chemical structure

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Part 2 of 2
Chemical structure
Glyoxal dimethyl acetal
PhH
RT, 18 h, 70%

See the Stork Enamine Synthesis
Chemical structure
  1. t-BuLi, CuCN
  2. TMSCl
Et2O, Et3N
-78 to -10 °C, 3 h, 93%

See the Michael Addition
Chemical structure
(CH2O)3, TiCl4
MeOH
-78 °C to RT, 16 h, 65%

See the Mukaiyama Aldol Addition
Chemical structure
  1. i-Pr2NLi
  2. PhNTf2
DME
-78 °C to RT, 4 h, 80%
Chemical structure + Chemical structure
Pd(PPh3)4, n-PrNH2, CuI
PhH
16 °C, 4 h, 76%

See the Sonogashira Coupling
Chemical structure
  1. Cy2BH
  2. AcOH
THF
0 °C to RT, 18.5 h, 70%
Chemical structure
(COCl)2, n-Bu3N
PhH, PhMe
RT to Reflux, 3 h, 71%
Chemical structure
Ph3COOH, NaOH
Acetone, H2O
-30 °C, 2 h, 86%

See the Baeyer-Villiger Oxidation
Chemical structure
HS(CH2)3SH, TiCl4
CH2Cl2
0 °C to RT, 50 min, 98%
Chemical structure
H2Cr2O7.2Pyr, AcOH
3 Å MS
CH2Cl2
0 °C, 60 min, 75%
Chemical structure
HIO4, H2O
CH2Cl2, MeOH
-30 °C to RT, 60 min, 80%
Chemical structure
Camphorsulfonic acid
MeOH
RT, 80%
Chemical structure
Reagent structure
Et2NLi
-25 to 0 °C, 45 min
Chemical structure
Camphorsulfonic acid
CH2Cl2
RT, 24 h, 75% (2 steps)
Chemical structure
NBS
CCl4
10 °C, 3 h

Selectivity : 10:60:30
See the Wohl-Ziegler Reaction
Chemical structure
+
Chemical structure
+
Chemical structure
AgNO3
MeCN
RT, 15 min, 50%

Also isolated were two allylic nitrates, both of which were converted to the desired product. The overall yield for these transformations is shown.
Chemical structure
Pyr.TsOH, Pyr
PhCl
135 °C, 16 h, 80%
Chemical structure
Ph3COOH, Et3NBn+ i-PrO-
THF
-10 °C, 3 h, 72%

See the Michael Addition
Chemical structure
EtCO2t-Bu, i-Pr2NLi
THF, HMPA
-78 to -30 °C, 12 h, 60%

See the Aldol Addition
Chemical structure
Camphorsulfonic acid
CH2Cl2
RT, 15 h, 82%
Chemical structure
TBSOTf, 2,6-Lutidine
MeCN
RT, 60 min, 89%
Chemical structure
OsO4
Pyr
Chemical structure
I2, CaCO3
MeOH
RT, 12 h, 40% (2 steps)
Chemical structure
BF3.OEt2
CH2Cl2
RT, 14 h, 89%
Chemical structure

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