Issue 5, 2012
From the journal:

Chemical Communications

Stereoselective synthesis of sugar fused β-disubstituted γ-butyro-lactones: C-spiro-glycosides from 1,2-cyclopropanecarboxylated sugars†

Perali Ramu Sridhar,*a   Kalapati Seshadria  and  Gadi Madhusudhan Reddya  

* Corresponding authors

a School of Chemistry, University of Hyderabad, Hyderabad, India
E-mail: prssc@uohyd.ernet.in
Fax: +91 4023012460
Tel: +91 4066794823

Abstract

A stereoselective methodology was developed for the construction of C-spiro-glycosides in two steps involving bromonium ion activated solvolytic ring opening of sugar derived 1,2-cyclopropanecarboxylates followed by a one-pot dehydrohalogenation, intramolecular hetero-Michael addition (IHMA) and ester hydrolysis. The obtained spirocyclic lactols were further converted to enantiomerically pure spirolactones.

Graphical abstract: Stereoselective synthesis of sugar fused β-disubstituted γ-butyro-lactones: C-spiro-glycosides from 1,2-cyclopropanecarboxylated sugars

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C1CC16417A
Article type
Communication
Submitted
15 Oct 2011
Accepted
16 Nov 2011
First published
16 Nov 2011

Chem. Commun., 2012,48, 756-758

Permissions

Request permissions

Stereoselective synthesis of sugar fused β-disubstituted γ-butyro-lactones: C-spiro-glycosides from 1,2-cyclopropanecarboxylated sugars

P. R. Sridhar, K. Seshadri and G. M. Reddy, Chem. Commun., 2012, 48, 756 DOI: 10.1039/C1CC16417A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements