Issue 19, 2013

Enantioselective total synthesis of virosaine A and bubbialidine

Abstract

The first enantioselective total syntheses of virosaine A and bubbialidine are described. Key transformations include the formation of a tetracyclic intermediate via an intramolecular aza-Michael addition, generation of a N-hydroxy-pyrrolidine through a Cope elimination and an intramolecular [1,3]-dipolar cycloaddition to generate a complex 7-oxa-1-azabicyclo[3.2.1]octane ring system.

Graphical abstract: Enantioselective total synthesis of virosaine A and bubbialidine

Supplementary files

Article information

Article type
Communication
Submitted
07 Dec 2012
Accepted
17 Jan 2013
First published
18 Jan 2013
This article is Open Access

Chem. Commun., 2013,49, 1921-1923

Enantioselective total synthesis of virosaine A and bubbialidine

H. Miyatake-Ondozabal, L. M. Bannwart and K. Gademann, Chem. Commun., 2013, 49, 1921 DOI: 10.1039/C3CC38783F

This is an Open Access article. The full version of this article can be posted on a website/blog, posted on an intranet, photocopied, emailed, distributed in a course pack or distributed in Continuing Medical Education (CME) materials provided that it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, 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 commercial 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