Synthesis of Trifarienol B

C15H26O2
Principal investigator | Toshio Honda |
---|---|
Publication year | 2009 |
Synthesis type | Partial |
Number of steps | 15 (linear) |
References |
Part 1 of 1

Et3N,
TMSCl
DMF
130 °C, 68 h
"The starting material is obtained in 5 steps from 2-methylcyclohexanone, see: Tetrahedron: Asymmetry 1995, 6, 1795."

LiAlH4
THF
0 °C, 40 min

BzCl,
Pyr
CH2Cl2
0 °C, 60 min, 77% (3 steps)



Et3N,
TMSOTf
CH2Cl2
0 °C to RT, 30 min, 94%



- TMS2NNa
- Comins' reagent
THF
-40 °C, 12 h, 69%




(CH2NMe2)2,
4-Methylbenzoyl chloride
CH2Cl2
0 °C to RT, 60 min, 98%

NMO,
OsO4
H2O, t-BuOH, THF
RT, 3 d, 64%
See the Upjohn Dihydroxylation
"Also isolated was the C-1 epimer (23 % yield)."

