Synthesis of Sumanene

Structure of Sumanene

C21H12

Principal investigatorHidehiro Sakurai
Publication year2003
Synthesis typeTotal
Number of steps 4 (linear)
References
Part 1 of 1
intermediate structure
  1. KOt-Bu
  2. n-BuLi
  3. n-Bu3SnCl
  4. Br(CH2)2Br
THF
-78 °C to RT, 17 h, 74%
intermediate structure
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%
intermediate structure
DDQ
PhMe
Reflux, 3 h, 70%
intermediate structure