Hirsutene

C₁₅H₂₄

Part 1 of 1

i-Pr₂NLi, TBSCl

THF, HMPA
-78 °C, 90 min

CHCl₃
Reflux, 5 h

See the Ireland-Claisen Rearrangement

PhSeCl

CH₂Cl₂
-78 °C, 25 min, 75 % (3 steps)

H₂O₂

THF, H₂O
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 %

n-Bu₄N⁺ I^-

PhH
Reflux, 2 h, 75 %

See the Finkelstein Reaction

Trimethylsilylacetylene, n-BuLi

THF, HMPA
0 °C, 20 min

n-Bu₄N⁺ F^-

THF
RT, 2 h, 75 % (2 steps)

n-Bu₃SnH, AIBN

PhH
Reflux, 60 min, 64 %