Synthesis of Grandisine D

C16H21NO2
Principal investigator | Osamu Tamura |
---|---|
Publication year | 2009 |
Synthesis type | Total |
Number of steps | 17 (linear) |
References |
Part 1 of 1
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AcCl
Reflux


Et3N
CH2Cl2
0 °C to RT, 5 h

AcCl
Reflux, 90 min, 90% (3 steps)

H2SO4,
NaBH4
EtOH, H2O
-52 °C to RT, 14 h, 84%



(CH2OH)2,
TsOH
PhH
Reflux, 13 h, 88%
"Also isolated was the C8a-epimer (8 % yield)."

NaOEt
EtOH
4 °C to RT, 10 h, 70%

DMAP,
PhOC(S)Cl
CH2Cl2
Reflux, 24 h, 100%


TsOH
Acetone, H2O
Reflux, 15 min, 97%




HClO4,
PhSH
H2O, MeOH
RT, 2 h, 94%


CH2Cl2, PhMe
65 °C, 15 min, 81%

Me3O+BF4-
MeCN
4 °C to RT, 60 min

NaBH3CN
MeOH
RT, 60 min, 63% (2 steps)
