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Named reactions

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Search synthesis

Elailoide

Chemical structure of Elailoide
C42H68O12
Author David A. Evans
Publication year 1997
Synthesis type Total synthesis
Number of steps 22 (2 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 2
Chemical structure
  1. i-Pr2NLi
  2. EtI
THF
-78 to 20 °C, 24 h, 82%
Chemical structure
TBSOTf, 2,6-Lutidine
CH2Cl2
0 °C, 60 min, 98%
Chemical structure
i-Bu2AlH
CH2Cl2
-78 to -40 °C, 90 min, 100%
Chemical structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C, 80 min, 100%

See the Swern Oxidation
Chemical structure + Chemical structure
BF3.OEt2
CH2Cl2
-78 °C, 45 min, 89%
Chemical structure
n-Bu4N+ F-
THF
RT, 10 min, 96%
Chemical structure
t-Bu2Si(OTf)2, 2,6-Lutidine
CH2Cl2
0 °C, 60 min, 91%
Chemical structure
  1. O3
  2. Me2S
CH2Cl2, MeOH
-78 °C to RT, 3 h, 90%
Chemical structure

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Part 2 of 2
Chemical structure
+
Chemical structure
n-Bu2BOTf, Et3N
CH2Cl2
-78 to 0 °C, 80 min, 86%

See the Evans Asymmetric Aldol Addition
Chemical structure
TESOTf, 2,6-Lutidine
CH2Cl2
0 °C, 30 min, 92%
Chemical structure
LiBH4
Et2O, H2O
RT, 3 h, 87%
Chemical structure
Ph3CCl, Et3N, DMAP
CH2Cl2
RT, 6 h, 92%
Chemical structure
  1. 9-BBN
  2. H2O2, H2O
THF
0 °C, 3 h, 89%
Chemical structure
(COCl)2, Et3N, DMSO
CH2Cl2
-78 °C, 70 min, 98%

See the Swern Oxidation
Chemical structure + Chemical structure
TMS2NLi
THF
-78 °C, 12 h, 85%

See the Horner-Wadsworth-Emmons Reaction
Chemical structure
Pyr.HF
THF
0 °C, 4 h, 93%
Chemical structure
KOH
THF, MeOH, H2O
RT, 98%
Chemical structure
Reagent structure
Et3N, DMAP
PhMe
RT, 105 min, 62%

See the Yamaguchi Esterification
Chemical structure
Camphorsulfonic acid
MeOH, THF
RT, 65%
Chemical structure
(COCl)2, Et3N, DMSO
CH2Cl2
-78 °C, 96%

See the Swern Oxidation
Chemical structure + Chemical structure
PhBCl2, i-Pr2NEt
CH2Cl2
-78 to 0 °C, 2.5 h, 66%

See the Aldol Addition
Chemical structure
Pyr.HF, Pyr
THF, H2O
RT, 3 h, 91%
Chemical structure

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