Synthesis of Brevisamide

Structure of Brevisamide

C18H29NO4

Principal investigatorArmen Zakarian
Publication year2011
Synthesis typeTotal
Number of steps 16 (linear)
References
Org. Lett. 2011, 13, 3636.
Part 1 of 1
intermediate structure
LiAlH4
Et2O
-78 °C to RT, 2 h, 89%
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 1 h
See the Swern Oxidation
intermediate structure
Ph3P, CBr4
CH2Cl2
0 °C, 45 min, 87% (2 steps)
See the Corey-Fuchs Reaction
intermediate structure
  1. n-BuLi
  2. MeI
THF, DMPU
-78 °C to RT, 3.5 h, 95%
See the Corey-Fuchs Reaction
intermediate structure
POCl3
DMF
RT, 24 h, 90%
See the Vilsmeier-Haack Formylation
intermediate structure
Special reagent
MeNO2, Cu(OAc)2
EtOH
RT, 5 d, 69%
See the Henry Reaction
">99:01 e.r."
intermediate structure
LiAlH4
THF
-15 °C to Reflux, 2.5 h
intermediate structure
Ac2O
EtOAc, MeOH
RT, 12 h, 67% (2 steps)
intermediate structure
NBS, NaOAc, NaHCO3
H2O, THF
0 °C, 90 min
See the Achmatowicz Reaction
intermediate structure
BF3.OEt2, Et3SiH
CH2Cl2
0 °C, 30 min, 54% (2 steps)
intermediate structure
MeLi, CuBr.Me2S
Et2O
-78 to 0 °C, 2 h, 55%
intermediate structure
NaBH4
H2O, THF
RT, 5 min, 43%
"Also isolated was the C-3 epimer (43% yield)"
intermediate structure
CuCN, PhMe2SiLi
Et2O, THF
-78 to 0 °C, 2.5 h, 93%
"93:07 mixture of regioisomers"
intermediate structure
2,6-Lutidine, NIS
HFIPA
0 °C, 5 min, 84%
"93:07 mixture of regioisomers"
intermediate structure
Special reagent
Pd2(dba)3, Ph3As, CuBr.Me2S
DMSO, THF
RT, 1 h, 78%
See the Stille Coupling
intermediate structure
PhI(OAc)2, TEMPO
CH2Cl2
RT, 2 h, 90%
intermediate structure
Report an error in this part