Isochroman- and 1,3-dihydroisobenzofuran-annulation on carbohydrate templates via [2+2+2]-cyclotrimerization and synthesis of some tricyclic nucleosides

TitleIsochroman- and 1,3-dihydroisobenzofuran-annulation on carbohydrate templates via [2+2+2]-cyclotrimerization and synthesis of some tricyclic nucleosides
Publication TypeJournal Article
Year of Publication2010
AuthorsSuryawanshi, SB, Dushing, MP, Gonnade, RG, Ramana, CV
JournalTetrahedron
Volume66
Issue32
Pagination6085-6096
Date PublishedAUG
ISSN0040-4020
KeywordsDihydroisobenzofuran, Dihydroisobenzopyran, Modified nucleosides, Vorbruggen reaction, [2+2+2] cyclotrimerization
Abstract

The synthesis of enantiopure tricyclic systems comprising isochroman or dihydroisobenzofuran units integrated with sugar templates has been documented. The alkyne cylotrimerization reaction has been employed with easily accessible sugar diynes for the key bicyclic ring construction and thus a provision to alter the functional groups on the newly formed aromatic rings. By selecting two representative trimerization products, we have synthesized the tricyclic nucleosides by simple synthetic manipulations. (c) 2010 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tet.2010.06.011
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

3.011

Divison category: 
Organic Chemistry