Synthesis of Bicyclohumulenone

Structure of Bicyclohumulenone

C15H24O

Principal investigator	André B. Charette
Publication year	1997
Synthesis type	Total
Number of steps	15 (linear)
References	Tetrahedron 1997, 53, 16277.

Part 1 of 1

intermediate structure

TMSCl, Na

PhMe

Reflux, 16 h, 82%

See the Acyloin Condensation

intermediate structure

HCl

H2O, THF

Reflux, 3 h, 80%

intermediate structure

LiAlH4

THF

Reflux, 12 h, 70%

intermediate structure

NaIO4

H2O, THF

RT, 24 h, 100%

intermediate structure

Special reagent

Reflux, 24 h

See the Wittig Reaction

intermediate structure

NaBH4, CeCl3.7H2O

MeOH

-78 °C, 45 min, 85%

See the Luche Reduction

intermediate structure

Imidazole, TBDPSCl

DMF

RT, 45 min, 66%

intermediate structure

Special reagent

CH2I2, Et2Zn

CH2Cl2, DME

0 °C to RT, 105 min, 88%

See the Charette Asymmetric Cyclopropanation

"94:06 e.r."

intermediate structure

Celite, H2Cr2O7.2Pyr

4 A MS

CH2Cl2

RT, 16 h, 100%

intermediate structure

i-Pr2NLi, EtOAc

THF

-78 to 0 °C, 75 min, 75%

See the Aldol Addition

intermediate structure

NMO, n-Pr4N+ RuO4-

4 A MS

CH2Cl2

RT, 30 min, 80%

See the Ley-Griffith Oxidation

intermediate structure

n-Bu4N+ F-

THF

RT, 5 h, 100%

intermediate structure

LiCl, MsCl, 2,4,6-Collidine

DMF

0 °C, 3 h

intermediate structure

Cs2CO3

DMF, THF

Reflux, 6 h, 85% (2 steps)

intermediate structure

KOH

DMF, H2O, MeOH

RT to 140 °C, 90 min, 100%

intermediate structure

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