Issue 30, 2012

Enantioselective synthesis of C-linked spiroacetal-triazoles as privileged natural product-like scaffolds

Abstract

The enantioselective synthesis of novel C-linked spiroacetal-triazoles 10 is reported. The key step involves reaction of acetylenic spiroacetal 11 with several azides by the Copper-Catalysed AzideAlkyne Cycloaddition (CuAAC). The biologically privileged spiroacetal scaffold 11 was prepared from silyl-protected Weinreb amide 19 using several reliable Grignard additions and a highly diastereoselective enzymatic kinetic resolution.

Graphical abstract: Enantioselective synthesis of C-linked spiroacetal-triazoles as privileged natural product-like scaffolds

Supplementary files

Article information

Article type
Paper
Submitted
27 10 2011
Accepted
30 11 2011
First published
01 12 2011

Org. Biomol. Chem., 2012,10, 5993-6002

Enantioselective synthesis of C-linked spiroacetal-triazoles as privileged natural product-like scaffolds

J. T. B. Kueh, K. W. Choi and M. A. Brimble, Org. Biomol. Chem., 2012, 10, 5993 DOI: 10.1039/C2OB06802H

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