Synthesis of Trifarienol B

Structure of Trifarienol B

C15H26O2

Principal investigatorToshio Honda
Publication year2009
Synthesis typePartial
Number of steps 15 (linear)
References
Part 1 of 1
intermediate 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."
intermediate structure
LiAlH4
THF
0 °C, 40 min
intermediate structure
BzCl, Pyr
CH2Cl2
0 °C, 60 min, 77% (3 steps)
intermediate structure
Pd(OAc)2, O2
DMSO
80 °C, 15 h, 91%
intermediate structure
MeLi, CuI
-78 to -40 °C, 80 min, 93%
intermediate structure
TMSOTf, Et3N
CH2Cl2
0 °C to RT, 30 min, 94%
intermediate structure
Pd(OAc)2, O2
DMSO
80 °C, 20 h, 75%
intermediate structure
VinylMgBr
THF
-78 to 0 °C, 12.5 h, 90%
intermediate structure
  1. TMS2NNa
  2. Comins' reagent
THF
-40 °C, 12 h, 69%
intermediate structure
TMSCH2MgCl, Pd2(dba)3, t-Bu3P
THF
Reflux, 12 h, 83%
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%
intermediate structure
4-Methylbenzoyl chloride, (CH2NMe2)2
CH2Cl2
0 °C to RT, 60 min, 98%
intermediate structure
OsO4, NMO
THF, t-BuOH, H2O
RT, 3 d, 64%
"Also isolated was the C-1 epimer (23 % yield)."
intermediate structure
SmI2
HMPA
RT, 5 min, 25%
intermediate structure