Erysodienone information

Erysodienone
Names
	IUPAC name 16-Hydroxy-3,15-dimethoxy-1,3,4,6-tetradehydroerythrinan-2-one
	Systematic IUPAC name (9bS)-7-Hydroxy-8,11-dimethoxy-1,2,4,5-tetrahydro-12H-indolo[7a,1-a]isoquinolin-12-one
Identifiers
CAS Number	5531-67-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	74174422;
PubChem CID	101277375;
	InChI InChI=1S/C18H19NO4/c1-22-16-9-13-11(7-14(16)20)3-5-19-6-4-12-8-15(21)17(23-2)10-18(12,13)19/h7-10,20H,3-6H2,1-2H3/t18-/m0/s1 Key: QVVZUVOFOCDCTO-SFHVURJKSA-N;
	SMILES COC1=C(C=C2CCN3CCC4=CC(=O)C(=C[C@@]43C2=C1)OC)O;
Properties
Chemical formula	C18H19NO4
Molar mass	313.353 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

Erysodienone is a key precursor in the biosynthesis of many Erythrina-produced alkaloids.^[1] Early work was done by Derek Barton and co-workers to illustrate the biosynthetic pathways towards erythrina alkaloids.^[2]^[3]^[4] It was demonstrated that erysodienone could be synthesized from simple starting materials by a similar approach as its biosynthetic pathway, which led to the development of the biomimetic synthesis of erysodienone.^[5]

^ Rahman, Mohammed Zakiur; J Sultana, Shirin; Faruquee, Chowdhury; Ferdous, Faisol; Rahman, Mohammad; S Islam, Mohammad; Rashid, Mohammad A (May 2007). "Phytochemical and Biological investigations of Erythrina variegata" (PDF). Saudi Pharmaceutical Journal. 15.
^ Barton, D. H. R.; Boar, R. B.; Widdowson, D. A. (January 1970). "Part XXI: The biosynthesis of the Erythrina alkaloids". Journal of the Chemical Society C: Organic. Phenol oxidation and biosynthesis. 9 (9): 1213–1218. doi:10.1039/J39700001213. ISSN 0022-4952. PMID 5463829.
^ Barton, Derek H. R.; Potter, Christopher J.; Widdowson, David A. (January 1974). "Part XXIII: On the benzyltetrahydroisoquinoline origins of the Erythrina alkaloids". Journal of the Chemical Society, Perkin Transactions 1. Phenol oxidation and biosynthesis: 346–348. doi:10.1039/P19740000346. ISSN 1364-5463.
^ Barton, D. H. R.; James, R.; Kirby, G. W.; Turner, D. W.; Widdowson, D. A. (January 1968). "Part XVIII: The structure and biosynthesis of Erythrina alkaloids". Journal of the Chemical Society C: Organic. Phenol oxidation and biosynthesis. 12: 1529–1537. doi:10.1039/J39680001529. ISSN 0022-4952. PMID 5690074.
^ Herbert, R. B. (1985). "The Biosynthesis of Isoquinoline Alkaloids". The Chemistry and Biology of Isoquinoline Alkaloids. Proceedings in Life Sciences. pp. 213–228. doi:10.1007/978-3-642-70128-3_14. ISBN 978-3-642-70130-6. ISSN 0172-6625.

[1] Rahman, Mohammed Zakiur; J Sultana, Shirin; Faruquee, Chowdhury; Ferdous, Faisol; Rahman, Mohammad; S Islam, Mohammad; Rashid, Mohammad A (May 2007). "Phytochemical and Biological investigations of Erythrina variegata" (PDF). Saudi Pharmaceutical Journal. 15.

[barton1970-2] Barton, D. H. R.; Boar, R. B.; Widdowson, D. A. (January 1970). "Part XXI: The biosynthesis of the Erythrina alkaloids". Journal of the Chemical Society C: Organic. Phenol oxidation and biosynthesis. 9 (9): 1213–1218. doi:10.1039/J39700001213. ISSN 0022-4952. PMID 5463829.

[3] Barton, Derek H. R.; Potter, Christopher J.; Widdowson, David A. (January 1974). "Part XXIII: On the benzyltetrahydroisoquinoline origins of the Erythrina alkaloids". Journal of the Chemical Society, Perkin Transactions 1. Phenol oxidation and biosynthesis: 346–348. doi:10.1039/P19740000346. ISSN 1364-5463.

[4] Barton, D. H. R.; James, R.; Kirby, G. W.; Turner, D. W.; Widdowson, D. A. (January 1968). "Part XVIII: The structure and biosynthesis of Erythrina alkaloids". Journal of the Chemical Society C: Organic. Phenol oxidation and biosynthesis. 12: 1529–1537. doi:10.1039/J39680001529. ISSN 0022-4952. PMID 5690074.

[Herbert1985-5] Herbert, R. B. (1985). "The Biosynthesis of Isoquinoline Alkaloids". The Chemistry and Biology of Isoquinoline Alkaloids. Proceedings in Life Sciences. pp. 213–228. doi:10.1007/978-3-642-70128-3_14. ISBN 978-3-642-70130-6. ISSN 0172-6625.