Stereoselective synthesis of tetrahydropyran–tetrahydrofuran (THP–THF) core of (+)-muconin via Prins cyclization

descriptionPublicationkeyboard_double_arrow_right Article 01 Jul 2014 English Publisher:Elsevier BVJournal:Tetrahedron Letters, volume 55, pages 3,860-3,863 (issn: 0040-4039,

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Authors: J.S. Yadav; U.V. Subba Reddy; B.V. Subba Reddy;

doi: 10.1016/j.tetlet.2014.02.096

Stereoselective synthesis of tetrahydropyran–tetrahydrofuran (THP–THF) core of (+)-muconin via Prins cyclization

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Abstract

Abstract A stereoselective synthesis of tetrahydropyran–tetrahydrofuran (THP–THF) core 2 of (+)-muconin (1) has been achieved using Prins cyclization as a key step to construct tetrahydropyran moiety. Other important transformations such as Wittig olefination, Sharpless epoxidation, regio-, and stereoselective exo-cyclization of the epoxy alcohol, titanocene induced regioselective deoxygenation of 2,3-epoxy alcohol, Grignard reaction, and Barton–McCombie reaction are successfully employed to accomplish the synthesis of THP–THF core 2.

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Indian Institute of Chemical Technology
India

5 Research products, page 1 of 1

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