Synthesis of Twistane

Structure of Twistane

C10H16

Principal investigator	Pierre Deslongchamps
Publication year	1967
Synthesis type	Total
Number of steps	7 (linear)
References	Can. J. Chem. 1967, 45, 297.

Part 1 of 1

intermediate structure

TsOH, HC(OEt)3

EtOH

-20 to 0 °C, 60 min, 65%

intermediate structure

Li

EtOH, NH3, THF

-33 °C, 60 min, 99%

intermediate structure

Pyr, MsCl

CH2Cl2

-10 °C, 24 h

intermediate structure

(CO2H)2

Et2O, H2O

RT, 2 h, 59% (2 steps)

intermediate structure

NaH

Dioxane

Reflux, 5 h, 85%

intermediate structure

(CH2SH)2, BF3.OEt2

AcOH

RT, 16 h, 100%

intermediate structure

Ni (Raney)

EtOH

Reflux, 5 h, 70%

intermediate structure

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