Aszonalenin

Aszonalenin

Names
IUPAC name (2R,10S,12R)-10-(2-methylbut-3-en-2-yl)-1,3,14-triazapentacyclo[10.9.0.02,10.04,9.015,20]henicosa-4,6,8,15,17,19-hexaene-13,21-dione[1]
Identifiers
CAS Number	81797-27-5
3D model (JSmol)	Interactive image
ChemSpider	28286412
PubChem CID	42636439
UNII	0V5DQ674AU
CompTox Dashboard (EPA)	DTXSID50398686
InChI InChI=1S/C23H23N3O2/c1-4-22(2,3)23-13-18-19(27)24-16-11-7-5-9-14(16)20(28)26(18)21(23)25-17-12-8-6-10-15(17)23/h4-12,18,21,25H,1,13H2,2-3H3,(H,24,27)/t18-,21-,23+/m1/s1 Key: AVLMMDWEIUEKEK-AAIMPIBUSA-N
SMILES CC(C)(C=C)[C@]12C[C@@H]3C(=O)NC4=CC=CC=C4C(=O)N3[C@H]1NC5=CC=CC=C25
Properties
Chemical formula	C23H23N3O2
Molar mass	373.456 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Aszonalenin is an alkaloid which is produced by Neosartorya and Aspergillus species.[2][3] Aszonalenin is a neurotoxin.[4]

References

1. "Aszonalenin". PubChem.
2. Whittall, John; Sutton, Peter W. (16 April 2012). Practical Methods for Biocatalysis and Biotransformations 2. John Wiley & Sons. p. 254. ISBN 978-1-119-94341-9.
3. Grundon, M. F. (1983). Alkaloids. Royal Society of Chemistry. p. 214. ISBN 978-0-85186-367-2.
4. Lubertozzi, David M. (2009). "Developing Aspergillus as a Host for Heterologous Expression". Biotechnology Advances. 27 (1). University of California, Berkeley: 53–75. doi:10.1016/j.biotechadv.2008.09.001. PMID 18840517.

Further reading

• Ruchti, Jonathan; Carreira, Erick M. (2014). "Ir-Catalyzed Reverse Prenylation of 3-Substituted Indoles: Total Synthesis of (+)-Aszonalenin and (–)-Brevicompanine B". J. Am. Chem. Soc. 136 (48): 16756–16759. doi:10.1021/ja509893s. PMID 25365411.
• Kimura, Yasuo; Hamasaki, Takashi; Nakajima, Hiromitsu; Isogai, Akira (1982). "Structure of aszonalenin, a new metabolite of Aspergillus zonatus". Tetrahedron Letters. 23 (2): 225–228. doi:10.1016/S0040-4039(00)86791-X. ISSN 0040-4039.