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Named reactions

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Search synthesis

Maritimol

Chemical structure of Maritimol
C20H34O2
Author Pierre Deslongchamps
Publication year 2000
Synthesis type Formal synthesis
Number of steps 27 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
+
Chemical structure
CrCl2, LiI
THF, DMF
RT, ON, 75%

See the Takai Reaction
Chemical structure
  1. i-Pr2NLi
  2. MeO2CCN
THF
-100 to 0 °C, 80 min, 90%
Chemical structure

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Part 2 of 3
Chemical structure
Me2SO4, NaH
DMSO
5 °C to RT, 4 h, 87%
Chemical structure
  1. O3
  2. Me2S
  3. NaBH4
CH2Cl2, MeOH
-78 °C to RT, 5 h, 73%
Chemical structure
TBSCl, Imidazole, DMAP
CH2Cl2
0 °C, 60 min, 95%
Chemical structure
NaOH
THF, H2O
5 °C, ON, 96%
Chemical structure
CDI, NHMeOMe, Et3N
CH2Cl2
0 °C to RT, ON, 89%
Chemical structure
i-Bu2AlH
CH2Cl2
-78 °C, 6 h, 89%
Chemical structure + Chemical structure
Pyr.TsOH
PhH
Reflux, 48 h, 93%
Chemical structure
TBDPSCl, Imidazole
CH2Cl2
RT, 30 min, 100%
Chemical structure + Chemical structure
i-Pr2NLi
-100 to 0 °C, 2 d, 83%
Chemical structure
MMPP
MeOH, Et2O
0 °C, 5 min, 98%
Chemical structure
Pyr.HF
THF
RT, 15 min, 76%
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
PdCl2.2MeCN
DMF
RT, ON, 68%

See the Stille Coupling
Chemical structure
Cl3CC(O)CCl3, Ph3P
CH2Cl2
-78 to 0 °C, 15 min, 94%

See the Appel Reaction
Chemical structure
Cs2CO3, CsI
Syringe pump
MeCN
80 °C, 14 h, 73%
Chemical structure
n-Bu4N+ F-
THF
0 °C to RT, 3 h, 87%
Chemical structure
Dess-Martin Periodinane
CH2Cl2
0 °C, 60 min, 91%

See the Dess-Martin Oxidation
Chemical structure
H2O
DMSO
155 °C, 3.5 h, 86%

See the Diels-Alder Reaction
Chemical structure
TMSCH2CN, n-BuLi, B(Oi-Pr)3
THF
-78 °C, 90 min, 67%

See the Peterson Olefination
Also isolated was the E-isomer (12 % yield).
Chemical structure
H2, Pd/C
1 atm
EtOAc, AcOH
RT, 4 h, 87%
Chemical structure
KOt-Bu
t-BuOH
85 °C, 2.5 h, 100%

See the Thorpe-Ziegler Reaction
Chemical structure
H3PO4
AcOH, H2O
110 °C, 37 h, 68%
Chemical structure
H2, Pt/C
40 atm
EtOAc
RT, 3 h
Chemical structure
Dess-Martin Periodinane
CH2Cl2
0 °C to RT, 10 h, 84% (2 steps)

See the Dess-Martin Oxidation
Chemical structure

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Remaining...
43% (2 steps)

See: Can. J. Chem. 1985, 63, 3418.
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