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Named reactions

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Trifarienol B

Chemical structure of Trifarienol_B
C15H26O2
Author Toshio Honda
Publication year 2009
Synthesis type Partial synthesis
Number of steps 15 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
TMSCl, Et3N
DMF
130 °C, 68 h

The starting material is obtained in 5 steps from 2-methylcyclohexanone, see: Tetrahedron: Asymmetry 1995, 6, 1795.
Chemical structure
LiAlH4
THF
0 °C, 40 min
Chemical structure
BzCl, Pyr
CH2Cl2
0 °C, 60 min, 77% (3 steps)
Chemical structure
Pd(OAc)2, O2
DMSO
80 °C, 15 h, 91%

See the Saegusa-Ito Oxidation
Chemical structure
MeLi, CuI
-78 to -40 °C, 80 min, 93%

Selectivity : 85:15 dr
See the Michael Addition
Chemical structure
TMSOTf, Et3N
CH2Cl2
0 °C to RT, 30 min, 94%

Selectivity : 85:15 dr
Chemical structure
Pd(OAc)2, O2
DMSO
80 °C, 20 h, 75%

See the Saegusa-Ito Oxidation
Chemical structure
Reagent structure
VinylMgBr
THF
-78 to 0 °C, 12.5 h, 90%

Selectivity : 83:17 dr
See the Michael Addition
Chemical structure
  1. TMS2NNa
  2. Comins' reagent
THF
-40 °C, 12 h, 69%

Selectivity : 83:17 dr
Chemical structure
TMSCH2MgCl, Pd2(dba)3, t-Bu3P
THF
Reflux, 12 h, 83%

See the Kumada-Corriu Coupling
Chemical structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 to 0 °C, 2.5 h, 98%

See the Swern Oxidation
Chemical structure
ZnCl2
CHCl3
Reflux, 30 min, 93%

See the Hosomi-Sakurai Reaction
Chemical structure
4-Methylbenzoyl chloride, (CH2NMe2)2
CH2Cl2
0 °C to RT, 60 min, 98%
Chemical structure
OsO4, NMO
THF, t-BuOH, H2O
RT, 3 d, 64%

See the Upjohn Dihydroxylation
Also isolated was the C-1 epimer (23 % yield).
Chemical structure
SmI2
HMPA
RT, 5 min, 25%

See the Markó-Lam Deoxygenation
Chemical structure

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