Synthesis of Quadrone

Structure of Quadrone

C15H20O3

Principal investigator	Eiichi Yoshii
Publication year	1983
Synthesis type	Formal
Number of steps	11 (linear)
References	J. Am. Chem. Soc. 1983, 105, 563.

Part 1 of 1

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+

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hν

CH2Cl2

-78 °C, 7 h, 67%

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i-Pr2NLi
TMSCl

THF

-78 °C to RT, 90 min, 98%

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CH2I2, Zn-Cu, MeOCH2Cl

CH2Cl2

0 °C to RT, 4.5 h, 60%

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Propargyl bromide, HgCl2, Al

Et2O, THF

-78 to -40 °C, 90 min, 50%

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HCO2H

RT, 40 h

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HCrO3Cl.Pyr

CH2Cl2

RT, 10 h, 31% (2 steps)

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HgO, H2SO4

H2O, MeOH

60 °C, 60 min, 100%

See the Kucherov Reaction

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NaOt-Amyl

PhH

Reflux, 3.5 h, 89%

See the Aldol Condensation

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BBr3

CH2Cl2

-78 to -20 °C, 24 h

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H2SO4, CrO3

Acetone, H2O

RT, 30 min, 49% (2 steps)

See the Jones Oxidation

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Remaining...

24% (5 steps)

"See : J. Am. Chem. Soc. 1981, 103, 4136."

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