Stereoselective synthesis of highly substituted 8-oxabicyclo[3.2.1]octanes and 2,7-dioxatricyclo[4.2.1.03,8]nonanes |
| |
Authors: | Dmitry A. Khlevin Sergey E. Sosonyuk Marina V. Proskurnina Nikolay S. Zefirov |
| |
Affiliation: | 1. Department of Chemistry, Moscow State Lomonosov University, Lenin Hills, 1, Moscow 119992, Russian Federation;2. Institute of Physiologically Active Compounds RAS, Severny proezd, 1, Chernogolovka 142432, Russian Federation |
| |
Abstract: | The synthesis of new polyhydroxylated 8-oxabicyclo[3.2.1]octanes and 2,7-dioxatricyclo[4.2.1.03,8]nonanes is described. These structures is an interesting synthetic blocks for potential bioactive molecules. The precursor, 3-chloro-8-oxabicyclo[3.2.1]oct-6-ene-2,4-dione was obtained from reaction of tetrachlorocyclopropene with furan, then it was involved in carbonyl groups reduction and double bond oxidation, resulted in the formation of a polyhydroxylated derivatives, differently substituted at C-3 position, with five new stereocenters.Using intramolecular transannular hydroxycyclization, bicyclic epoxy diacetate was transformed into 2,7-dioxatricyclo[4.2.1.03,8]nonane in high yield through an alkoxide intermediate. Compounds thus obtained have a structure close to certain molecules with antitumor and glycosidase inhibitors activity. |
| |
Keywords: | |
本文献已被 ScienceDirect 等数据库收录! |
|