Studies towards the total synthesis of Herbimycin A

Favier, Guillaume Marcel Olivier (2013) Studies towards the total synthesis of Herbimycin A. Doctoral thesis (PhD), University of Sussex.

[img]
Preview
PDF - Published Version
Download (6MB) | Preview

Abstract

Herbimycin A (1) belongs to the ansamycin family and is a 19-membered lactam with seven stereogenic centres, making it a synthetic challenge, which was first isolated in 1979 by Omura et al. Herbimycin A (1) exhibits a broad spectrum of biological activities: herbicidal, inhibitor of angiogenesis and of the maturation of growth factor receptor tyrosine kinases.

Figure 1 - Herbimycin A (for figure see pdf)

Since its discovery, only three total syntheses of Herbimycin A (1) have been described in the literature, along with the syntheses of advanced fragments.

This thesis describes a new route to Herbimycin A (1), using a wide range of chemical reactions than those used in the previous routes from the literature.

The main idea is to split Herbimycin A (1) into an aromatic fragment and an aliphatic fragment as shown below in Scheme 1.

Scheme 1 - Retrosynthesis highlighting both aromatic and aliphatic fragments (for figure see pdf)

The synthesis of aliphatic fragment (4) follows up the work of Ansell and Pietsch, past members of the Parsons group.
Interesting results could be obtained and a wide range of Organic Chemistry reactions could be investigated.

Item Type: Thesis (Doctoral)
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science > QD Chemistry > QD0241 Organic chemistry
Depositing User: Library Cataloguing
Date Deposited: 03 May 2013 13:11
Last Modified: 08 Sep 2015 14:55
URI: http://sro.sussex.ac.uk/id/eprint/44591

View download statistics for this item

📧 Request an update