Chemistry:Glionitrin A

From HandWiki
Glionitrin A
Glionitrin A structure.svg
Names
IUPAC name
(3R,10aR)-3-(hydroxymethyl)-2-methyl-7-nitro-2,3-dihydro-10H-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione
Identifiers
3D model (JSmol)
ChemSpider
Properties
C13H11N3O5S2
Molar mass 353.37 g·mol−1
Appearance Yellow powder
Melting point 181-182 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Glionitrin A is an antibiotic-anticancer compound made by microbes found in an abandoned mine.[1] The total synthesis of (−)-glionitrin A was reported by Daniel Strand and co-workers in 2021.[2]

References

  1. Park, H. B.; Kwon, H. C.; Lee, C. H.; Yang, H. O. (February 2009). "Glionitrin A, an antibiotic-antitumor metabolite derived from competitive interaction between abandoned mine microbes". J. Nat. Prod. 72 (2): 248–52. doi:10.1021/np800606e. PMID 19159274. 
  2. Koning, N.R.; Sundin, A.P.; Strand, D. (22 November 2021). "Total Synthesis of (−)-Glionitrin A and B Enabled by an Asymmetric Oxidative Sulfenylation of Triketopiperazines". J. Am. Chem. Soc. 143 (50): 21218–21222. doi:10.1021/jacs.1c10364. PMID 34808045.