CSIRO Publishing

An international journal for chemical science

Shopping Cart: ( empty )

RESEARCH FRONT

Previous Next Contents Vol 62(7)

Naturally Occurring Nitrogen–Sulfur Compounds. The Benzothiazole Alkaloids

Lucille Le Bozec ^A and Christopher J. Moody ^A ^B

+ Author Affiliations

- Author Affiliations

^A School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK.

^B Corresponding author. Email: c.j.moody@nottingham.ac.uk

Australian Journal of Chemistry 62(7) 639-647 https://doi.org/10.1071/CH09126
Submitted: 2 March 2009 Accepted: 16 March 2009 Published: 13 July 2009

Abstract

Several alkaloids contain both nitrogen and sulfur, and a subset of these interesting terrestrial and marine natural products – the benzothiazoles – forms the subject of the present short review. Benzothiazole alkaloids are relatively rare in Nature, but they range in structural complexity from benzothiazole itself and simple derivatives thereof, through the well-known firefly luciferin, to more complex molecules such as the thiazo-rifamycins and the dercitin-kuanoniamine family. Although the biosynthesis of benzothiazoles has not been studied in many cases, the evidence suggests that they are derived from cysteine addition to benzoquinone derivatives followed by ring contraction of the resulting benzothiazine adducts. The review also highlights the fact that little synthetic work has been done on benzothiazole-containing natural products.

References

[1] R. A. Hughes, C. J. Moody, Angew. Chem. Int. Ed. 2007, 46, 7930.
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | CAS |
        | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |
        | CAS |
        | Crossref | GoogleScholarGoogle Scholar | CAS |

^* Dercitin is occasionally spelt as dercitine in the literature; for consistency, we use dercitin throughout.