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Named reactions

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Stigmatellin A

"Dedicated to Professor Gerhard Höfle on the occasion of his 60th birthday."

Chemical structure of Stigmatellin_A
C30H42O7
Author Dieter Enders
Publication year 2000
Synthesis type Total synthesis
Number of steps 22 (4 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 4
Chemical structure
P2O5, H3PO4
EtCO2H
70 °C, 60 min, 73%

See the Friedel-Crafts Acylation
Chemical structure
mCPBA, CF3CO2H
CH2Cl2
5 °C, 16 h, 87%

See the Baeyer-Villiger Oxidation
Chemical structure
HCl
MeOH, H2O
Reflux, 2 h, 99%
Chemical structure
MeOCH2Cl, i-Pr2NEt
CH2Cl2
0 °C to RT, ON, 98%
Chemical structure

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Part 2 of 4
Chemical structure
4-Methoxyphenol, DEAD, Ph3P
CH2Cl2
0 °C to RT, 3 d, 95%

See the Mitsunobu Reaction
Chemical structure
NaI
Acetone
Reflux, 5 d, 83%

See the Finkelstein Reaction
Chemical structure + Chemical structure
i-Pr2NLi
Et2O
-100 °C to RT, ON, 80%

Selectivity : >99:01 dr
Chemical structure
MMPP
MeOH, Buffer (pH = 7)
-15 °C, 15 min, 87%
Chemical structure + Chemical structure
TiCl4, i-Pr2NEt
CH2Cl2
-78 °C to RT, 3.5 h, 64%

Selectivity : >99:01 dr
See the Aldol Addition
Chemical structure
Me4N+ BH(OAc)3-, AcOH
MeCN
-40 to -20 °C, 3 d, 99%

See the Evans-Saksena Reduction
Chemical structure
  1. KH, 18-Crown-6
  2. MeI
THF
0 °C to RT, 2 d, 77%

See the Williamson Ether Synthesis
Chemical structure
(NH4)2Ce(NO3)6
MeCN, H2O
0 °C, 6 min, 90%
Chemical structure
H2Cr2O7.2Pyr
DMF
RT, ON, 100%
Chemical structure

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Part 3 of 4
Chemical structure
+
Chemical structure
NaH
THF
-78 °C to RT, ON, 71%

See the Horner-Wadsworth-Emmons Reaction
Chemical structure
i-Bu2AlH
Et2O
-78 °C, 60 min, 99%
Chemical structure
PBr3
Et2O
0 °C, ON, 93%
Chemical structure
P(OEt)3
160 °C, ON, 63%

See the Michaelis-Arbuzov Reaction
Chemical structure

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Part 4 of 4
Chemical structure
+
Chemical structure
t-BuCOCl, i-Pr2NEt, DMAP
CH2Cl2
RT, 3.5 h, 57%
Chemical structure
NaOMe
MeOH
Reflux, 2 h, 75%

See the Baker-Venkataraman Rearrangement
Chemical structure
H2, Pd/C
1 atm
MeOH
RT, 6 min, 74%
Chemical structure
(COCl)2, DMSO, i-Pr2NEt
CH2Cl2
-78 °C to RT, 40 min

See the Swern Oxidation
Chemical structure + Chemical structure
i-Pr2NLi
THF
-78 °C to RT, ON, 77% (2 steps)

See the Horner-Wadsworth-Emmons Reaction
Chemical structure

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