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Named reactions

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Aigialomycin D

"We dedicate this article to Professor Richard J. K. Taylor in celebration of his 60th birthday."

Chemical structure of Aigialomycin_D
C18H22O6
Author Joanne E. Harvey
Publication year 2009
Synthesis type Total synthesis
Number of steps 20 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
  1. NaH
  2. n-BuLi
THF
-78 °C to Reflux, 51 h, 40 %
Chemical structure
Ac2O, Et3N
CH2Cl2
RT, 12 h, 98 %
Chemical structure
NBS, Bz2O2
CCl4
Reflux, 6 h, 71 %

See the Wohl-Ziegler Reaction
Chemical structure

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Part 2 of 3
Chemical structure
HCl
Acetone, MeOH
Reflux, 8 h, 55 %
Chemical structure
TsCl
Pyr
0 °C to RT, 15 h, 84 %
Chemical structure
NaI
MEK
Reflux, 24 h, 99 %

See the Finkelstein Reaction
Chemical structure
Zn, AcOH
MeOH
Reflux, 8 h
Chemical structure
+
Chemical structure
MeOH
0 °C to RT, 12 h, 74 % (2 steps)

Selectivity : 82:18 Z/E
See the Wittig Reaction
Chemical structure
NaBH4, CuCl, Cyclohexene
MeOH
-78 °C, 60 min, 96 %
Chemical structure
LiAlH4
Et2O
-10 °C, 10 min, 97 %
Chemical structure
MsCl, Et3N, DMAP
CH2Cl2
0 °C to RT, 12 h, 97 %
Chemical structure
KSAc
DMF
0 °C to RT, 12 h, 90 %
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
K2CO3
MeOH
RT, 12 h, 86 %
Chemical structure
MeOCH2Cl, NaH
DMF
0 °C to RT, 2 h, 74 %
Chemical structure
KOH
MeOH, H2O
90 °C, 48 h, 98 %
Chemical structure
+
Chemical structure
Ph3P, DIAD
THF
0 °C to RT, 2.5 h, 94 %

See the Mitsunobu Reaction
Chemical structure
mCPBA
CH2Cl2
0 °C to RT, 2 h, 84 %
Chemical structure
Grubbs-Hoveyda catalyst (2nd gen.)
µW
CH2Cl2
75 °C, 30 min, 86 %

See the Olefin Metathesis
Chemical structure
KOH, CCl4
CH2Cl2, t-BuOH
RT to 35 °C, 32 min, 84 %

See the Ramberg-Bäcklund Reaction
Chemical structure
HCl
MeOH, H2O
RT, 3 d, 85 %
Chemical structure

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