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Yaequinolone J1

Yaequinolone J1 is an antibiotic made by Penicillium.[1]

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
ChemSpider
  • 9830053
  • 11655315
  • 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
  • O=C4Nc2c(c1O[C@@](/C=C\c1cc2)(C)CC\C=C(/C)C)[C@](O)(c3ccc(OC)cc3)[C@H]4OC
Properties
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).

Total syntheses of yaequinolone J1 edit

An asymmetric total synthesis of yaequinolone J1 has been published in 2018 by V. Vece, S. Jakkepally and S. Hanessian.[2] In 2020, a five-step synthesis of yaequinolone J1 was reported.[3]

References edit

  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.


yaequinolone, antibiotic, made, penicillium, names, iupac, name, hydroxy, methoxy, methoxyphenyl, methyl, methyl, penten, tetrahydro, pyrano, quinolin, identifiers, model, jsmol, interactive, image, chemspider, 9830053, pubchem, 11655315, inchi, inchi, c27h31n. Yaequinolone J1 is an antibiotic made by Penicillium 1 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 ChemSpider 9830053 PubChem CID 11655315 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 s1Key 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 C 27H 31N O 5 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 referencesTotal syntheses of yaequinolone J1 editAn asymmetric total synthesis of yaequinolone J1 has been published in 2018 by V Vece S Jakkepally and S Hanessian 2 In 2020 a five step synthesis of yaequinolone J1 was reported 3 References edit 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 nbsp This systemic antibiotic related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Yaequinolone J1 amp oldid 1190984054, wikipedia, wiki, book, books, library,

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