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

Suryawanshi, Sharad B. ; Dushing, Mangesh P. ; Gonnade, Rajesh G. ; Ramana, C. V. (2010) The isochroman- and 1,3-dihydroisobenzofuran-annulation on carbohydrate templates via [2+2+2]-cyclotrimerization and synthesis of some tricyclic nucleosides Tetrahedron, 66 (32). pp. 6085-6096. ISSN 0040-4020

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.tet.2010.06.011

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.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Dihydroisobenzopyran; Dihydroisobenzofuran; [2+2+2] Cyclotrimerization; Modified Nucleosides; Vorbrüggen Reaction
ID Code:106047
Deposited On:01 Feb 2018 16:54
Last Modified:01 Feb 2018 16:54

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