Synthesis of Quadrone

Structure of Quadrone

C15H20O3

Principal investigator	Steven D. Burke
Publication year	1982
Synthesis type	Formal
Number of steps	21 (linear)
References	J. Am. Chem. Soc. 1982, 104, 872. J. Org. Chem. 1981, 46, 2400.

Part 1 of 1

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+

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THF

-78 °C to RT, 4.5 h, 77%

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LiAlH4

Et2O

0 °C, 4 h, 99%

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VinylOEt, Hg(OAc)2

Reflux, ON

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Sealed tube

187 to 200 °C, 6 h, 94% (2 steps)

See the Claisen Rearrangement

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CrO3, H2SO4

Acetone, H2O

0 °C to RT, 8.5 h, 98%

See the Jones Oxidation

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(COCl)2

PhH

RT, 8.5 h

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TiCl4

CH2Cl2

-30 °C to RT, 16 h, 84% (2 steps)

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NMO, OsO4

Acetone, H2O

See the Upjohn Dihydroxylation

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NaIO4

H2O, THF

94% (2 steps)

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TsOH, Morpholine

PhH

Reflux, 92%

See the Michael Addition

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Dibenzo-18-crown-6, NaOH

PhH

Reflux, 96%

See the Claisen-Schmidt Condensation

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TsOH, (CH2OH)2

PhH

Reflux

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NaOH, t-BuOOH

H2O, MeOH

RT, 89% (2 steps)

See the Michael Addition

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NH2NH2

AcOH, MeOH

92%

See the Wharton Reaction

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VinylOEt, Hg(OAc)2

Sealed tube

Xylene(s)

250 °C, 90%

See the Claisen Rearrangement

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H2, Pd/C

1 atm

EtOH

RT, 100%

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KOAc

Ac2O

Reflux

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OsO4, NaIO4

H2O, THF

57% (2 steps)

See the Lemieux-Johnson Oxidation

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CrO3, H2SO4

H2O

See the Jones Oxidation

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CH2N2

Et2O

60% (2 steps)

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Remaining...

24% (6 steps)

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

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