Synthesis of Trifarienol B

Structure of Trifarienol B

C15H26O2

Principal investigatorToshio Honda
Publication year2009
Synthesis typePartial
Number of steps 15 (linear)
References
J. Org. Chem. 2009, 74, 3424. Angew. Chem. Int. Ed. 2008, 47, 131.
Part 1 of 1
intermediate structure
Et3N, TMSCl
DMF
130 °C, 68 h
"The starting material is obtained in 5 steps from 2-methylcyclohexanone, see: Tetrahedron: Asymmetry 1995, 6, 1795."
intermediate structure
LiAlH4
THF
0 °C, 40 min
intermediate structure
BzCl, Pyr
CH2Cl2
0 °C, 60 min, 77% (3 steps)
intermediate structure
O2, Pd(OAc)2
DMSO
80 °C, 15 h, 91%
See the Saegusa-Ito Oxidation
intermediate structure
CuI, MeLi
-78 to -40 °C, 80 min, 93%
See the Michael Addition
intermediate structure
Et3N, TMSOTf
CH2Cl2
0 °C to RT, 30 min, 94%
intermediate structure
Pd(OAc)2, O2
DMSO
80 °C, 20 h, 75%
See the Saegusa-Ito Oxidation
intermediate structure
Special reagent
VinylMgBr
THF
-78 to 0 °C, 12.5 h, 90%
See the Michael Addition
intermediate structure
  1. TMS2NNa
  2. Comins' reagent
THF
-40 °C, 12 h, 69%
intermediate structure
Pd2(dba)3, TMSCH2MgCl, t-Bu3P
THF
Reflux, 12 h, 83%
See the Kumada-Corriu Coupling
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 to 0 °C, 2.5 h, 98%
See the Swern Oxidation
intermediate structure
ZnCl2
CHCl3
Reflux, 30 min, 93%
See the Hosomi-Sakurai Reaction
intermediate structure
(CH2NMe2)2, 4-Methylbenzoyl chloride
CH2Cl2
0 °C to RT, 60 min, 98%
intermediate structure
NMO, OsO4
H2O, t-BuOH, THF
RT, 3 d, 64%
See the Upjohn Dihydroxylation
"Also isolated was the C-1 epimer (23 % yield)."
intermediate structure
SmI2
HMPA
RT, 5 min, 25%
See the Markó-Lam Deoxygenation
intermediate structure
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