Synthesis of Panacene

Structure of Panacene

C15H15BrO2

Principal investigator	Ken S. Feldman
Publication year	1982
Synthesis type	Total
Number of steps	13 (linear)
References	J. Am. Chem. Soc. 1982, 104, 4011.

Part 1 of 1

intermediate structure

+

intermediate structure

NaH

DMF

See the Williamson Ether Synthesis

intermediate structure

NaH

PhH

81% (2 steps)

See the Claisen Condensation

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

Et3N, DMSO, (COCl)2

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

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