The photocycloaddition reactions of uridine and related compounds with 2,3-dimethyl-2-butene

DOI: 10.1248/cpb.39.1922

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1922 - 1930 (1991)

Update date:2022-09-26

Topics:

Authors:

Ishikawa

Itoh Itoh

Takayanagi

Oshima Oshima

Kawahara

Mizuno Mizuno

Ogura Ogura

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Article abstract of DOI:10.1248/cpb.39.1922

The photochemical reactions of uracil and 5-fluorouracil derivatives with simple alkenes have been investigated. Photocycloaddition of uracil or 5-fluorouracil derivatives and 2,3-dimethyl-2-butene in acetone gave an enantiomeric mixture of cross cycloadducts (4, 7) in moderate yields. Under similar conditions, diastereomers of 4-substituted 7,7,8,8-tetramethyl-cis-2,4-diazabicyclo[4.2.0]octane-3,5-dione nucleosides (14-17) were formed from uridine or 5-fluorouridine derivatives in good yields. The structures and stereochemistry of these cycloadducts of the nucleoside series were elucidated on the basis of the proton nuclear magnetic resonance spectra and X-ray crystallographic analysis.

Full text of DOI:10.1248/cpb.39.1922

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