C-Nucleosides and related compounds. VI. Carbocyclic analogues of C-nucleosides: synthesis and derivatives of some useful intermediates
- 15 March 1976
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 54 (6) , 849-860
- https://doi.org/10.1139/v76-123
Abstract
The Diels-Alder adduct of cyclopentadiene and .beta.-bromo acrylic acid (1) was converted to D,L-exo-6,7-(dihydroxy-di-O-isopropylidene)-2-hydroxy-3-oxabicyclo[3.2.1]octane (9) in an 8-step sequence and a 24% yield based on 1. Alternatively, the hemiacetal (9) was obtained in 5 steps and 22% yield from norbornadiene through the intermediate lactone. The thiosemicarbazone and semicarbazone of 9 were prepared. The synthesis of the free aldehyde and that of the Wittig reaction products are described.This publication has 0 references indexed in Scilit: