Yaequinolone J1

Yaequinolone J1
Names
	IUPAC name (2S,9R,10R)-10-Hydroxy-9-methoxy-10-(4-methoxyphenyl)-2-methyl-2-(4-methyl-3-penten-1-yl)-2,7,9,10-tetrahydro-8H-pyrano[2,3-f]quinolin-8-one
Identifiers
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:215148;
ChemSpider	9830053;
PubChem CID	11655315;
CompTox Dashboard (EPA)	DTXSID701028416 ;
	InChI InChI=1S/C27H31NO5/c1-17(2)7-6-15-26(3)16-14-18-8-13-21-22(23(18)33-26)27(30,24(32-5)25(29)28-21)19-9-11-20(31-4)12-10-19/h7-14,16,24,30H,6,15H2,1-5H3,(H,28,29)/t24-,26-,27+/m0/s1 Key: CPWPNTRWIIAFEG-DOEKTCAHSA-N;
	SMILES O=C4Nc2c(c1O[C@@](/C=C\c1cc2)(C)CC\C=C(/C)C)[C@](O)(c3ccc(OC)cc3)[C@H]4OC;
Properties
Chemical formula	C27H31NO5
Molar mass	449.547 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

Yaequinolone J1 is an antibiotic made by Penicillium.

Total syntheses of yaequinolone J1

An asymmetric total synthesis of yaequinolone J1 has been published in 2018 by V. Vece, S. Jakkepally and S. Hanessian. In 2020, a five-step synthesis of yaequinolone J1 was reported.

References

^ Uchida, R; Imasato, R; Shiomi, K; Tomoda, H; Omura, S (2005). "Yaequinolones J1 and J2, novel insecticidal antibiotics from Penicillium sp. FKI-2140". Org Lett. 7 (25): 5701–4. doi:10.1021/ol052458h. PMID 16321026.
^ Vece, V; Jakkepally, S; Hanessian, S (2018). "Total Synthesis and Absolute Stereochemical Assignment of the Insecticidal Metabolites Yaequinolones J1 and J2". Org. Lett. 20 (14): 4277–4280. doi:10.1021/acs.orglett.8b01701. PMID 29975546. S2CID 49710214.
^ Schwan, J; Kleoff, M; Heretsch, P; Christmann, M (2020). "Five-Step Synthesis of Yaequinolones J1 and J2". Org. Lett. 22 (2): 475–479. doi:10.1021/acs.orglett.9b04455. PMID 31909626.

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[1] Uchida, R; Imasato, R; Shiomi, K; Tomoda, H; Omura, S (2005). "Yaequinolones J1 and J2, novel insecticidal antibiotics from Penicillium sp. FKI-2140". Org Lett. 7 (25): 5701–4. doi:10.1021/ol052458h. PMID 16321026.

[2] Vece, V; Jakkepally, S; Hanessian, S (2018). "Total Synthesis and Absolute Stereochemical Assignment of the Insecticidal Metabolites Yaequinolones J1 and J2". Org. Lett. 20 (14): 4277–4280. doi:10.1021/acs.orglett.8b01701. PMID 29975546. S2CID 49710214.

[3] Schwan, J; Kleoff, M; Heretsch, P; Christmann, M (2020). "Five-Step Synthesis of Yaequinolones J1 and J2". Org. Lett. 22 (2): 475–479. doi:10.1021/acs.orglett.9b04455. PMID 31909626.