Synthesis of Longifolene

Structure of Longifolene

C15H24

Principal investigator	Arthur G. Schultz
Publication year	1985
Synthesis type	Formal
Number of steps	14 (linear)
References	J. Org. Chem. 1985, 50, 915.

Part 1 of 1

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+

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K

NH3, t-BuOH, THF

-78 °C, 98%

See the Birch Reduction

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HCl

MeOH

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ClCO2Me, NaHCO3

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HCl, HC(OMe)3

MeOH

Reflux

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NaOMe

MeOH

75% (4 steps)

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NBS

MeOH

95%

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DBU

PhMe

Reflux, 85%

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TsOH

Acetone

Reflux, 86%

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+

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Xylene(s)

Reflux, 40% (2 steps)

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Pd/C, H2

EtOH

RT, 92%

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KOH

H2O, MeOH

RT, 85%

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PhMe

Reflux, 86%

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Remaining...

75% (3 steps)

"See : J. Am. Chem. Soc. 1978, 100, 2583."

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