Hirsutene

Part 1 of 1

AgBF₄

CH₂Cl₂, DCE
-50 °C to RT, 20 h, 38 %

See the Nazarov Cyclization Reaction

MeLi

Et₂O
-78 °C, 4 h

HgCl₂, HgO, H₂SO₄

THF, H₂O
RT, 14 h, 94 % (2 steps)

t-BuLi, CuI, BF₃^.OEt₂

Et₂O, HMPT
-120 to -20 °C, 9 h, 60 %

See the Michael Addition
The yield was 74 % brsm.

KF^.2H₂O, Et₃NBn⁺ Cl^-

MeCN
60 °C, 10 h, 84 %

TsCl, Et₃N

CH₂Cl₂
RT, 94 %

TMS₂NLi

Et₂O
-78 to -30 °C, 4 h, 75 %

NaBH₄

MeOH
0 °C, 100 %

NaH, CS₂, MeI, Imidazole

THF
RT to 50 °C, 92 %

n-Bu₃SnH, AIBN

PhH
Reflux, 2 h, 70 %

See the Barton-McCombie Reaction