Hirsutene

Part 1 of 1

HC(OEt)₃, TsOH

EtOH
Reflux, 6 h, 95 %

O₃, Ph₃P

CH₂Cl₂
-78 °C to RT, ON, 100 %

PhH
RT to Reflux, 6 h, 81 %

See the Wittig Reaction

LiAlH₄

Et₂O
0 °C, 6 h, 99 %

HCl

THF, H₂O
RT, 25 min, 100 %

Pyrrolidine, Na₂S₂O₄

MeOH
RT, 24-36 h, 99 %

LiAlH₄

THF
RT, 6 h, 93 %

Mesitylene
Reflux, 24 h, 70 %

See the Diels-Alder Reaction

CrO₃, H₂SO₄

Acetone, H₂O
0 °C, 60 min, 97 %

See the Jones Oxidation

O₃, Me₂S

CH₂Cl₂
-78 °C to RT, 99 %

Ac₂O, Et₃N, DMAP

CH₂Cl₂
RT, 4 h, 90 %

CrO₃, H₂SO₄

Acetone, H₂O
RT, 45 min, 95 %

See the Jones Oxidation

(COCl)₂, DMF

PhH
RT, 2 h

t-BuSH, DMAP

PhMe
Reflux, 45 min, 82 % (2 steps)

See the Barton Decarboxylation

Et₃N

MeOH, H₂O
RT, 60 min, 95 %

Ph₃P⁺CH₃ Br^-, TMS₂NK

THF
0 °C to RT, 30 min, 86 %

See the Wittig Reaction

(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 %

KOH, n-Bu₄N⁺ OH^-

THF, Et₂O
Reflux, ON, 97 %

See the Aldol Condensation

H₂, PtO₂
1 atm

EtOAc
RT, 20 min, 100 %

Ph₃P⁺CH₃ Br^-, KH

PhH, t-BuOH
RT to Reflux, 6 h, 93 %

See the Wittig Reaction