4,9-Dimethoxynaphtho[2,3-b]furan 9 was obtained in 91% yield via the r
eductive methylation of naphtho[2,3-b]furan-4,9-dione 2. After treatme
nt of 9 with butyllithium, the mixture was allowed to react with N,N-d
imethylacetamide, followed by oxidization with cerium(IV) diammonium n
itrate to give 2-acetylnaphtho[2,3-b]furan-4,9-dione 1. 2-Formylnaphth
o[2,3-b]furan-4,9-dione 13 and 2-trimethylsilylnaphtho[2,3-b]furan-4,9
-dione 14 were also obtained from 9 by a similar method. The halodesil
ylations of 14 easily gave 2-iodonaphtho[2,3-b]furan-4,9-dione 16, 2-b
romonaphtho[2,3-b]furan-4,9-dione 17, and 2-chloronaphtho[2,3-b]furan-
4,9-dione 18 in 82%, and 93% and 83% yield, respectively. Furthermore,
the nitrodesilylation of 14 gave 2-nitronaphtho[2,3-b]furan-4,9-dione
3 in 77% yield.