Publication Cover
Natural Product Research
Formerly Natural Product Letters
Volume 33, 2019 - Issue 19
203
Views
1
CrossRef citations to date
0
Altmetric
Research Articles

A novel semi-synthesis of spinetoram-J based on the selective hydrolysis of 5,6-dihydro spinosyn A

ORCID Icon, ORCID Icon &
Pages 2801-2808 | Received 02 Jun 2018, Accepted 17 Jul 2018, Published online: 16 Nov 2018

References

  • Bacci L, Lupi D, Savoldelli S, Rossaro B. 2016. A review of Spinosyns a derivative of biological acting substances as a class of insecticides with a broad range of action against many insect pests. J Entomol Acarol Res. 48(1):40–52.
  • Baker PJ. 1993. Process for isolating A83543 and its components. U.S. Patent 5 227 295.
  • Boeck LD, Chio EH, Eaton TE, Godfrey OW, Michel KH, Nakatsukasa WM, Yao RC. 1990. Macrolide compounds. European Patent EP 0375316.
  • Chai HX, Shi DX, Zhang Q, Li JR. 2011. Recent advances in the insecticide of Spinosyns. Chem Ind Eng Prog. 30:239–243.
  • Cleveland CB, Mayes MA, Cryer SA. 2002. An ecological risk assessment for spinosad use on cotton. Pest Manag Sci. 58(1):70–84.
  • Creemer LC, Kirst HA, Paschal JW. 1998. Conversion of spinosyn A and spinosyn D to their respective 9- and 17-pseudoaglycones and their aglycones. J Antibiot. 51(8):795–799.
  • Crouse GD, Sparks TC, Schoonover J, Gifford J, Dripps J, Bruce T, Larson LL, Garlich J, Hatton C, Hill RL, et al. 2001. Recent advances in the chemistry of spinosyns. Pest Manag Sci. 57(2):177–185.
  • Mertz FP, Yao RC. 1990. Saccharopolyspora spinosa sp. nov. Isolated from soil collected in a sugar mill rum still. Int J Syst Bacteriol. 40(1):34–39.
  • Mynderse JS, Baker PJ, Mabe JA, Broughton MC, Huber MB, Martin JW, Turner JR. 1994. New A83543 compounds and process for production thereof. WO 9 420 518.
  • Oliver MP, Crouse GD, Demeter DA, Sparks TC. 2015. Synthesis and Insecticidal activity of spinosyns with C9-O-benzyl bioisosteres in place of the 2',3',4'-Tri-O-methyl rhamnose. J Agric Food Chem. 63(23):5571–5577.
  • Salgado VL, Sheets JJ, Watson GB, Schmidt AL. 1998. Studies on the mode of action of spinosad: insect symptoms and physiological correlates. Pestic Biochem Physiol. 60(2):91–110.
  • Sparks TC, Thompson GD, Kirst HA, Hertlein MB, Larson LL, Worden TV, Thibault ST. 1998. Biological activity of the spinosyns new fermentation derived insect control agents on tobacco budworm (Lepidoptera: Noctuidae) larvae. J Economic Entomol. 91(6):1277–1283.
  • Sparks TC, Crouse GD, Dripps JE, Anzeveno P, Martynow J, Deamicis CV, Gifford J. 2008. Neural network-based QSAR and insecticide discovery: spinetoram. J Comput Aided Mol Des. 22(6-7):393–401.
  • Thompson GD, Dutton R, Sparks TC. 2000. Spinosad: a case study: an example from a natural products discovery programme. Pest Manag Sci. 56(8):696–702.
  • Thompson GD, Sparks TC. 2002. Spinosad: a green natural product for insect control. Chapter 5. In: Advancing sustainability through green chemistry and engineering. Washington DC: American Chemical Society; pp. 61–73.
  • Tillman PG, Mulrooney JE. 2000. Effect of selected insecticides on the natural enemies Coleomegilla maculata and Hippodamia convergens (Coleoptera: Coccinellidae) Geocoris punctipes (Hemiptera: Lygaeidae) and Bracon mellitor Cardiochiles nigriceps and Cotesia marginiventris (Hymenoptera: Braconidae) in cotton. EC. 93(6):1638–1643.
  • Turner JR, Huber MLB, Broughton MC, Mynderse JS, Martin JW. 1997. Process for the production of A83543 compounds with Saccharopolyspora spinosa. U.S. Patent 5 591 606.
  • Yang CD, Song LH. 2007. Analyses of spinosad and its degradates from light irradiation. Chem J Chinese U. 28:2056–2059.
  • Zhang K, Liu SL, Liu AJ, Chai HX, Li JR, A LMS. 2017. A semisynthesis of 3'-O-ethyl-5,6-dihydrospinosyn J based on the spinosyn A aglycone. Beilstein J Org Chem. 13:2603–2609.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.