Issue 7, 2015

Synthesis of biologically active natural products, aspergillides A and B, entirely from biomass derived platform chemicals

Abstract

The depletion of finite fossil fuels drives the need to develop sustainable chemical feedstock such as biomass. The synthesis of biologically active natural products aspergillides A and B was achieved whereby all the carbon atoms present originated from biomass derived platform chemicals such as ethanol, levulinic acid and 5-hydroxymethylfurfural (HMF). The key steps in this synthesis include Noyori's asymmetric transfer hydrogenation, Achmatowicz rearrangement coupled with a triple reduction sequence, micellar Negishi coupling as well as an enzymatic kinetic resolution. Lipshutz's micellar Negishi coupling was also successfully applied on an advanced synthetic intermediate for the first time with good yield and excellent selectivity. This synthesis demonstrates the feasibility of constructing biologically active compounds using a sustainable chemical feedstock like biomass.

Graphical abstract: Synthesis of biologically active natural products, aspergillides A and B, entirely from biomass derived platform chemicals

Supplementary files

Article information

Article type
Communication
Submitted
28 Apr 2015
Accepted
18 May 2015
First published
18 May 2015

Green Chem., 2015,17, 3746-3750

Author version available

Synthesis of biologically active natural products, aspergillides A and B, entirely from biomass derived platform chemicals

P.-F. Koh and T.-P. Loh, Green Chem., 2015, 17, 3746 DOI: 10.1039/C5GC00900F

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