Synthesis of Sumanene

Structure of Sumanene

C21H12

Principal investigator	Hidehiro Sakurai
Publication year	2003
Synthesis type	Total
Number of steps	4 (linear)
References	Science 2003, 301, 1878.

Part 1 of 1

intermediate structure

KOt-Bu , n-BuLi
Br(CH2)2Br
n-Bu3SnCl

THF

-78 °C to RT, 17 h, 74%

intermediate structure

Special reagent

NMP

-78 °C to RT, 13 h, 16%

"Also isolated was the syn:anti diastereoisomer (47 % yield)."

intermediate structure

Grubbs catalyst (1st gen.), C2H4

PhMe

RT, 24 h, 30%

See the Olefin Metathesis

intermediate structure

DDQ

PhMe

Reflux, 3 h, 70%

intermediate structure

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