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Named reactions

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Zaragozic Acid C

Chemical structure of Zaragozic_Acid_C
C40H50O14
Author David A. Evans
Publication year 1994
Synthesis type Total synthesis
Number of steps 29 (3 parts)
References

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
+
Chemical structure
n-Bu2BOTf, Et3N
CH2Cl2
-78 to -40 °C, 2.5 h, 96%

See the Evans Asymmetric Aldol Addition
Chemical structure
TBSOTf, 2,6-Lutidine
CH2Cl2
0 °C, 60 min
Chemical structure
LiBH4
THF, MeOH
0 °C, 3.5 h
Chemical structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 to 0 °C, 90 min, 92% (3 steps)

See the Swern Oxidation
Chemical structure

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Part 2 of 3
Chemical structure
AllylMgBr
THF
0 °C, 93%

See the Weinreb Ketone Synthesis
Chemical structure
Et2BOMe, NaBH4
MeOH, AcOH
85%

See the Narasaka-Prasad Reduction
Chemical structure
2,2-Dimethoxypropane, Pyr.TsOH
PhH
98%
Chemical structure
Li
NH3, THF
-60 °C, 100%

See the Birch Reduction
Chemical structure
"This iodide was readily prepared from intermediates previously reported by us"
Chemical structure

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Part 3 of 3
Chemical structure
Cyclopentanone dimethyl acetal, TsOH
PhH
65 °C, 12 h, 85%
Chemical structure
  1. TMS2NLi
  2. TMSCl
THF
-78 to 0 °C, 60 min, 97%
Chemical structure + Chemical structure
i-PrOTiCl3
CH2Cl2
-78 to -40 °C, 4.5 h, 76%

See the Mukaiyama Aldol Addition
Chemical structure
Dess-Martin Periodinane, Pyr
CH2Cl2
RT, 8 h, 94%

See the Dess-Martin Oxidation
Chemical structure
VinylMgBr
CH2Cl2, THF
-78 °C, 10 h, 76%

See the Grignard Reaction
Chemical structure
OsO4, NMO
t-BuOH, THF, H2O
40 h

See the Upjohn Dihydroxylation
Chemical structure
Pb(OAc)4
PhH
20 min

See the Criegee Reaction
Chemical structure
n-Pr4N+ RuO4-, NMO
4 Å MS
CH2Cl2
RT, 5 h, 84% (3 steps)

See the Ley-Griffith Oxidation
Chemical structure
  1. O3, Pyr
  2. Me2S
CH2Cl2
-78 °C to RT, 4 h
Chemical structure
NaClO2, NaH2PO4, 2-Methyl-2-butene
t-BuOH
3.5 h

See the Pinnick-Lindgren Oxidation
Chemical structure
N,N'-diisopropyl-O-tert-butylisourea
CH2Cl2
24 h, 91% (3 steps)
Chemical structure + Chemical structure
t-BuLi
Hexane(s), Et2O
-78 °C, 20 min, 73%
Chemical structure
DDQ
CH2Cl2
60 min
Chemical structure
Ac2O, DMAP
PhH, Pyr
90% (2 steps)
Chemical structure
H2O
CF3CO2H, CH2Cl2
Chemical structure
N,N'-diisopropyl-O-tert-butylisourea
CH2Cl2
24 h, 52% (2 steps)
Chemical structure
H2, Pd/C
50 atm
MeOH, AcOH
20 h, 96%
Chemical structure + Chemical structure
DCC, DMAP
CH2Cl2
36 h, 82%

See the Steglich Esterification
Chemical structure
n-Bu4N+ F-
THF
0 °C, 15 min, 99%
Chemical structure
CF3CO2H
CH2Cl2
24 h, 99%
Chemical structure

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