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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 18, Number 7
BKCSDE 18(7)
July 20, 1997 

A Synthetic Approach to 11-Oxabicyclo[6.2.1]undecyl Bicyclics
Hee-Sun Jeong, Hun Kim, Ho-Jung Kang*
Through a sequence of reactions including Diels-Alder cycloaddition of a furan diene as the key step, 11-oxatricyclo[,6]undecyl rings were synthesized from 5-methylfurfural with the goal of developing a synthetic protocol to 11-oxabicyclo[6.2.1]undecyl system. The strategy to incorporate an oxygen atom at C6 carbon of tricyclic 11 or 16 by Baeyer-Villiger oxidation was unsuccessful, implicating that there is too much steric congestion around the carbonyl ketone. As an alternative approach, bicyclic 23 and 24 were prepared from 2-methylfuran via known tricyclic 20. Cyclization of bicyclic 23 and 24 under several reaction conditions also failed to produce hydroxylated product 25 and 26.
754 - 760
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