Stereocontrolled total synthesis of (+)-concanamycin F: the strategic use of boron-mediated aldol reactions of chiral ketones
Paterson, Ian; Doughty, Victoria A; McLeod, Malcolm; Trieselmann, Thomas
Description
A highly stereocontrolled total synthesis of the 18-membered macrolide (+)-concanamycin F, a potent inhibitor of vacuolar ATPases, is described that proceeds in 5.8% yield over 26 steps. The three key fragments, C1-C13 vinyl iodide, C14-C22 vinyl stannane and C23-C28 aldehyde, were efficiently constructed using asymmetric boron-mediated aldol reactions of appropriate chiral ketone building blocks. The nature of the silyl protection of the C7/C9 hydroxyls proved to be critical for achieving...[Show more]
Collections | ANU Research Publications |
---|---|
Date published: | 2011 |
Type: | Journal article |
URI: | http://hdl.handle.net/1885/60536 |
Source: | Tetrahedron |
DOI: | 10.1016/j.tet.2011.09.012 |
Download
File | Description | Size | Format | Image |
---|---|---|---|---|
01_Paterson_Stereocontrolled_total_2011.pdf | 1.28 MB | Adobe PDF | Request a copy |
Items in Open Research are protected by copyright, with all rights reserved, unless otherwise indicated.
Updated: 20 July 2017/ Responsible Officer: University Librarian/ Page Contact: Library Systems & Web Coordinator