Synthesis of Hirsutene

C15H24
Principal investigator | Daniel D. Sternbach |
---|---|
Publication year | 1990 |
Synthesis type | Total |
Number of steps | 22 (linear) |
References |
Part 1 of 1
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TsOH,
HC(OEt)3
EtOH
Reflux, 6 h, 95%

- O3
- Ph3P
CH2Cl2
-78 °C to RT, ON, 100%



LiAlH4
Et2O
0 °C, 6 h, 99%

HCl
H2O, THF
RT, 25 min, 100%


Na2S2O4,
Pyrrolidine
MeOH
RT, 24-36 h, 99%

LiAlH4
THF
RT, 6 h, 93%



- O3
- Me2S
CH2Cl2
-78 °C to RT, 99%

Et3N,
DMAP,
Ac2O
CH2Cl2
RT, 4 h, 90%


(COCl)2,
DMF
PhH
RT, 2 h


Et3N
H2O, MeOH
RT, 60 min, 95%


(COCl)2,
NaH
PhH
RT, 4 h

Me2CuLi
Et2O
-78 to 0 °C, 60 min, 97% (2 steps)

- O3
- Me2S
CH2Cl2
-78 °C to RT, 80%


H2,
PtO2
1 atm
EtOAc
RT, 20 min, 100%

