Synthesis of Brevisamide

C18H29NO4
Principal investigator | Armen Zakarian |
---|---|
Publication year | 2011 |
Synthesis type | Total |
Number of steps | 16 (linear) |
References |
Part 1 of 1

LiAlH4
Et2O
-78 °C to RT, 2 h, 89%






LiAlH4
THF
-15 °C to Reflux, 2.5 h

Ac2O
EtOAc, MeOH
RT, 12 h, 67% (2 steps)


BF3.OEt2,
Et3SiH
CH2Cl2
0 °C, 30 min, 54% (2 steps)

MeLi,
CuBr.Me2S
Et2O
-78 to 0 °C, 2 h, 55%

NaBH4
H2O, THF
RT, 5 min, 43%
"Also isolated was the C-3 epimer (43% yield)"

CuCN,
PhMe2SiLi
Et2O, THF
-78 to 0 °C, 2.5 h, 93%
"93:07 mixture of regioisomers"

2,6-Lutidine,
NIS
HFIPA
0 °C, 5 min, 84%
"93:07 mixture of regioisomers"


PhI(OAc)2,
TEMPO
CH2Cl2
RT, 2 h, 90%
