Synthesis of Triquinacene

Structure of Triquinacene

C10H10

Principal investigator	Robert B. Woodward
Publication year	1964
Synthesis type	Total
Number of steps	16 (linear)
References	J. Am. Chem. Soc. 1964, 86, 3162.

Part 1 of 1

intermediate structure

CrO3.2Pyr

74%

See the Sarett Oxidation

intermediate structure

NaOAc, AcOOH

AcOH, CH2Cl2

92%

See the Prilezhaev Reaction

intermediate structure

KOt-Bu

Et2O, THF

90%

intermediate structure

CrO3

Et2O, H2O

70%

intermediate structure

Pb(OAc)4

PhH

intermediate structure

MeOH

45% (2 steps)

intermediate structure

CH2N2

intermediate structure

NaOMe

MeOH

intermediate structure

NaOH

H2O, MeOH

67% (3 steps)

intermediate structure

SOCl2

intermediate structure

NaN3

PhMe

See the Curtius Rearrangement

intermediate structure

MeOH

84% (3 steps)

intermediate structure

LiAlH4

THF

84%

intermediate structure

CH2O

H2O, HCO2H

94%

See the Eschweiler-Clarke Reaction

intermediate structure

H2O2

H2O, MeOH

intermediate structure

125-140 °C, 78% (2 steps)

See the Cope Elimination

intermediate structure

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