Synthesis of Triquinacene

Structure of Triquinacene

C10H10

Principal investigator	James M. Cook
Publication year	1989
Synthesis type	Total
Number of steps	8 (linear)
References	J. Am. Chem. Soc. 1989, 111, 2169.

Part 1 of 1

intermediate structure

+

intermediate structure

K2CO3, NaHCO3

H2O, MeOH

RT, 3 d, 45%

See the Weiss-Cook Condensation

intermediate structure

CH2N2

CH2Cl2

RT, 2 h, 90%

intermediate structure

Allyl-I, KH

DMF

-58 to -25 °C, 6 h

intermediate structure

HCl

AcOH, H2O

Reflux, 90 min, 90% (2 steps)

intermediate structure

O3
Me2S

EtOAc

-58 °C, 81%

intermediate structure

HCl

H2O, THF

RT, 7 d, 86%

See the Aldol Addition

intermediate structure

BH3.THF

THF

0 °C, 16 h, 93%

intermediate structure

HMPA

Reflux, 2 d, 80%

intermediate structure

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