Regioselective Epoxide Ring Opening. Steroselective Synthesis of a Tetrahydropyran Ring

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Abstract

The stereoselective synthesis of a 2-substituted tetrahydropyran with adjacent alkoxy-bearing stereogenic centre is described. The key steps of this synthesis were the stereoselective epoxidation of an allylic alcohol and the regioselective epoxide ring opening by lithium aluminum hydride. The regio and stereoselective synthesis of a trihydroxyselenide and a trihydroxysulfide is also described. The latter compounds are not suitable for cyclization to tetrahydrofuran ring.
Original languageEnglish
Pages (from-to)865-869
Number of pages5
JournalJOURNAL OF HETEROCYCLIC CHEMISTRY
Volume35
Publication statusPublished - 1998

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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