Synthesis of Hirsutene
C15H24
Principal investigator | Dennis P. Curran |
---|---|
Publication year | 1985 |
Synthesis type | Total |
Number of steps | 12 (linear) |
References |
Part 1 of 1
+
- i-Pr2NLi
- TBSCl
HMPA, THF
-78 °C, 90 min
PhSeCl
CH2Cl2
-78 °C, 25 min, 75% (3 steps)
H2O2
H2O, THF
0 °C, ON, 82%
Li.Naphthalene,
CuBr.Me2S
THF, Me2S
-78 to -20 °C, 5.5 h
Pyr.TsOH
EtOH
Reflux, 4 h, 75% (2 steps)
i-Bu2AlH
THF
-78 °C to RT, 7 h, 83%
Tf2O,
Pyr
CH2Cl2
-10 °C, 70 min, 81%
Trimethylsilylacetylene,
n-BuLi
HMPA, THF
0 °C, 20 min
n-Bu4N+ F-
THF
RT, 2 h, 75% (2 steps)
n-Bu3SnH,
AIBN
PhH
Reflux, 60 min, 64%