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Stereoselective synthesis of tetrahydropyran–tetrahydrofuran (THP–THF) core of (+)-muconin via Prins cyclization.
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Jul2014, Vol. 55 Issue 29, p3860-3863. 4p. - Publication Year :
- 2014
-
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. [Copyright &y& Elsevier]
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 55
- Issue :
- 29
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 96784628
- Full Text :
- https://doi.org/10.1016/j.tetlet.2014.02.096