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Named reactions

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Search synthesis

Okilactomycin

Chemical structure of Okilactomycin
C24H32O6
Author Amos B. Smith, III
Publication year 2007
Synthesis type Total synthesis
Number of steps 37 (3 parts)
References

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
+
Chemical structure
i-Pr2NLi, LiCl
THF
-78 °C to RT, 24 h, 95%

See the Myers Asymmetric Alkylation
Chemical structure
i-Pr2NLi, BH3.NH3
THF
0 °C to RT, 3 h, 94%
Chemical structure
Pyr.SO3, DMSO, Et3N
CH2Cl2
0 °C, 30 min, 90%

See the Parikh-Doering Oxidation
Chemical structure
Ph3P+CH3 Br-, n-BuLi
THF
0 °C, 3 h, 96%

See the Wittig Reaction
Chemical structure
n-Bu4N+ F-
THF
0 °C to RT, 5 h, 97%
Chemical structure
Pyr.SO3, DMSO, Et3N
CH2Cl2
0 °C, 30 min, 93%

See the Parikh-Doering Oxidation
Chemical structure + Chemical structure
n-Bu2BOTf, Et3N
CH2Cl2
-78 to 0 °C, 3.5 h, 93%

See the Evans Asymmetric Aldol Addition
Chemical structure
LiOH, H2O2
H2O
0 °C to RT, 2 h, 97%
Chemical structure

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Part 2 of 3
Chemical structure
+
Chemical structure
PhMe
90 °C, 24 h, 88%

Selectivity : 89:11 (Endo:Exo)
See the Diels-Alder Reaction
Chemical structure
LiAlH4
Et2O
-78 °C to RT, 90 min, 97%
Chemical structure
  1. TMS2NNa
  2. BnBr, n-Bu4N+ I-
THF
0 °C to RT, 70 min

See the Williamson Ether Synthesis
Chemical structure
HF
MeCN
RT, 60 min, 90% (2 steps)
Chemical structure
  1. Li(s-Bu)3BH
  2. PhNTf2
THF
-78 °C to RT, 7.5 h, 82%
Chemical structure
CO, Pd(PPh3)4, n-Bu3SnH, LiCl
THF
70 °C, 5 h, 87%
Chemical structure
Reagent structure
CH2Cl2
-78 °C, 60 min, 71%
Chemical structure
  1. KH, 18-Crown-6
  2. Me2SO4
THF
0 °C to RT, 22 h, 96%

See the Cope Rearrangement
Chemical structure
mCPBA
MeOH
0 °C, 30 min, 91%

See the Rubottom Oxidation
Chemical structure
  1. NaH
  2. 2-Bromomethylnaphthalene, n-Bu4N+ I-
DMF
0 °C to RT, 36 h, 96%

See the Williamson Ether Synthesis
Chemical structure
  1. Cp2ZrHCl
  2. NBS
CH2Cl2
0 °C to RT, 40 min, 98%
Chemical structure
PhSeH, Cs2CO3
MeCN
RT, 60 min, 93%
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
i-PrOTMS, TMSOTf
CH2Cl2
0 °C, 30 min
Chemical structure
Cp2TiMe2
THF
60 °C, 24 h

See the Tebbe-Petasis Olefination
Chemical structure
Me2AlCl
CH2Cl2
RT, 5 min, 42% (3 steps)

See the Petasis-Ferrier Rearrangement
Chemical structure
Reagent structure
Pyr
CHCl3
RT to 60 °C, 2.5 h, 94%
Chemical structure
DDQ
CH2Cl2, MeOH
RT, 60 min, 84%
Chemical structure
  1. TMS2NK
  2. ClCO2Me
THF
-78 to 0 °C, 65 min, 99%
Chemical structure
NaOMe
THF
0 °C, 60 min
Chemical structure
MeI, K2CO3
MeCN
70 °C, 2 h, 88% (2 steps)
Chemical structure
Grubbs-Hoveyda catalyst (2nd gen.)
PhH
80 °C, 24 h

See the Olefin Metathesis
Chemical structure
H2, Pd/C
1 atm
EtOAc
RT, 15 h, 84% (2 steps)
Chemical structure
  1. o-NO2PhSeCN, n-Bu3P
  2. H2O2, H2O
THF, Pyr
0 °C to RT, ON, 90%

See the Grieco Dehydration
Chemical structure
SeO2, t-BuOOH
CH2Cl2
10 °C, 40 min, 54%

The yield was 62 % brsm.
Chemical structure
SOCl2, Propylene oxide
Et2O
0 °C, 4 h, 74%
Chemical structure
  1. TMS2NNa
  2. PhSeCl
THF
-78 °C, 30 min, 83%
Chemical structure
Et3NO
DMSO
RT, 12 h, 65%

See the Ganem Oxidation
Chemical structure
NaIO4
THF, H2O
RT, 5 h, 90%
Chemical structure
NaClO2, NaH2PO4, 2-Methyl-2-butene
THF, t-BuOH, H2O
RT, 60 min, 80%

See the Pinnick-Lindgren Oxidation
Chemical structure

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