Synthesis of Panacene

Structure of Panacene

C15H15BrO2

Principal investigatorKen S. Feldman
Publication year1982
Synthesis typeTotal
Number of steps 13 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
NaH
DMF
intermediate structure
NaH
PhH
81% (2 steps)
intermediate structure
AllylBr, NaH
DMF
intermediate structure
HCl
MeOH
intermediate structure
K(s-Bu)3BH
THF
63% (3 steps)
intermediate structure
NBS
MeCN
intermediate structure
KOAc
DMF
intermediate structure
NaOMe
MeOH
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
See the Swern Oxidation
intermediate structure + intermediate structure
THF
intermediate structure
n-Bu4N+ F-
THF
15% (2 steps)
"Also isolated was the epimer (10 % yield)."
intermediate structure
MsCl, Et3N
CH2Cl2
intermediate structure
LiCuBr2
THF
69% (2 steps)
intermediate structure