Issue 20, 2011
From the journal:

Chemical Communications

Noteworthy observations accompanying synthesis of the apoptolidin disaccharide†

Madduri Srinivasarao,b   Taesik Park,b   Yuzhong Chenb  and  Philip L. Fuchs*a  

* Corresponding authors

a Department of Chemistry, Purdue University, West Lafayette, USA
E-mail: pfuchs@purdue.edu
Tel: +1-765-494-5242

b Department of Chemistry, Purdue University, West Lafayette, USA

Abstract

A stereoselective synthesis of the apoptolidin disaccharide is reported. The key chemistry features a new transformation utilizing a highly selective tetramethylalkoxyalanate[V]-directedsyn-methylation of a vinylogous ester, isolation of a hydrate of a 2-keto sugar, an eco-friendly radical cleavage of a bromomethyl group, and an efficient preparation of a fluorodisaccharidevia the use of XtalFluor-E.

Graphical abstract: Noteworthy observations accompanying synthesis of the apoptolidin disaccharide

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Article information

DOI
https://doi.org/10.1039/C1CC11448D
Article type
Communication
Submitted
13 Mar 2011
Accepted
29 Mar 2011
First published
18 Apr 2011

Chem. Commun., 2011,47, 5858-5860

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Noteworthy observations accompanying synthesis of the apoptolidin disaccharide

M. Srinivasarao, T. Park, Y. Chen and P. L. Fuchs, Chem. Commun., 2011, 47, 5858 DOI: 10.1039/C1CC11448D

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