Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigatorPhilip Magnus
Publication year1985
Synthesis typeTotal
Number of steps 10 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
AgBF4
DCE, CH2Cl2
-50 °C to RT, 20 h, 38%
intermediate structure
MeLi
Et2O
-78 °C, 4 h
intermediate structure
H2SO4, HgCl2, HgO
H2O, THF
RT, 14 h, 94% (2 steps)
intermediate structure + intermediate structure
BF3.OEt2, CuI, t-BuLi
Et2O, HMPT
-120 to -20 °C, 9 h, 60%
"The yield was 74 % brsm."
intermediate structure
Et3NBn+ Cl-, KF.2H2O
MeCN
60 °C, 10 h, 84%
intermediate structure
Et3N, TsCl
CH2Cl2
RT, , 94%
intermediate structure
TMS2NLi
Et2O
-78 to -30 °C, 4 h, 75%
intermediate structure
NaBH4
MeOH
0 °C, , 100%
intermediate structure
  1. Imidazole
  2. MeI
  3. NaH
  4. CS2
THF
RT to 50 °C, , 92%
intermediate structure
AIBN, n-Bu3SnH
PhH
Reflux, 2 h, 70%
intermediate structure