Kendomycin

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title: "Kendomycin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["macrolides", "antibiotics", "quinone-methides", "total-synthesis"] topic_path: "general/macrolides" source: "https://en.wikipedia.org/wiki/Kendomycin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 387363125 | Reference= | ImageFile = Kendomycin.svg | ImageClass = skin-invert-image | IUPACName = (1R,9S,10S,12S,14E,16S,19R,20R,21S,22R)-3,9,21-Trihydroxy-5,10,12,14,16,20,22-heptamethyl-23,24-dioxatetracyclo[17.3.1.16,9.02,7]tetracosa-2,5,7,14-tetraen-4-one | SystematicName = (1R,9S,10S,12S,14E,16S,19R,20R,21S,22R)-3,9,21-Trihydroxy-5,10,12,14,16,20,22-heptamethyl-23,24-dioxatetracyclo[17.3.1.16,9.02,7]tetracosa-2,5,7,14-tetraen-4-one | OtherNames=(-)-TAN 2162 |Section1={{Chembox Identifiers | CASNo_Ref = | CASNo=59785-91-0 | PubChem=5472093 | ChEMBL_Ref = | ChEMBL = 523927 | ChemSpiderID_Ref = | ChemSpiderID = 4582118 | SMILES = C[C@H]\1CC[C@@H]2C@@HC | InChI = 1/C29H42O6/c1-14-8-9-22-18(5)24(30)19(6)28(34-22)23-21-13-29(33,17(4)12-16(3)11-15(2)10-14)35-27(21)20(7)25(31)26(23)32/h10,13-14,16-19,22,24,28,30,32-33H,8-9,11-12H2,1-7H3/b15-10+/t14-,16+,17-,18-,19+,22+,24-,28+,29+/m0/s1 | InChIKey = HKLDUJXJTQJSEJ-OLXNOMCWBE | StdInChI_Ref = | StdInChI = 1S/C29H42O6/c1-14-8-9-22-18(5)24(30)19(6)28(34-22)23-21-13-29(33,17(4)12-16(3)11-15(2)10-14)35-27(21)20(7)25(31)26(23)32/h10,13-14,16-19,22,24,28,30,32-33H,8-9,11-12H2,1-7H3/b15-10+/t14-,16+,17-,18-,19+,22+,24-,28+,29+/m0/s1 | StdInChIKey_Ref = | StdInChIKey = HKLDUJXJTQJSEJ-OLXNOMCWSA-N | RTECS = | MeSHName = C485395 |Section2={{Chembox Properties | Formula=C29H42O6 | MolarMass=486.64 g/mol | Appearance=Yellow powder | Density= | MeltingPt= | BoilingPt= | Solubility= | SolubleOther = Soluble | Solvent = DMSO, methanol |Section3={{Chembox Hazards | MainHazards=Toxic | FlashPt= | AutoignitionPt =

Kendomycin is an anticancer macrolide first isolated from Streptomyces violaceoruber. It has potent activity as an endothelin receptor antagonist and anti-osteoporosis agent. It also has strong cytotoxicity against various tumor cell lines.

Total synthesis

Because of its potent biological activities, kendomycin has attracted interest as a target of total synthesis. The first total synthesis of kendomycin was accomplished by Lee and Yuan in 2004. The total number of syntheses stands at 6.

References

References

  1. [http://www.alexis-biochemicals.com/Kendomycin.5+M5acc5c8c65d.0.html Kendomycin] {{Webarchive. link. (2008-05-16 at Alexis-Biochemicals)
  2. (2000). "Structure and biosynthesis of kendomycin, a carbocyclic ansa-compound from Streptomyces". J. Chem. Soc. Perkin Trans. 1.
  3. [http://www.chem.wisc.edu/~burke/Kendo.htm Burke Research Group] {{Webarchive. link. (2006-08-29 University of Wisconsin)
  4. (2004). "Total Synthesis of Kendomycin: A Macro−C−Glycosidation Approach". J. Am. Chem. Soc..
  5. (2006). "Evolution of a Total Synthesis of (−)-Kendomycin Exploiting a Petasis−Ferrier Rearrangement/Ring-Closing Olefin Metathesis Strategy". J. Am. Chem. Soc..
  6. (2008). "Total Synthesis of (−)-Kendomycin". Org. Lett..
  7. J. Am. Chem. Soc.. (2008). "Formal Synthesis of (−)-Kendomycin Featuring a Prins-Cyclization to Construct the Macrocycle"
  8. (2009). "Total Synthesis of the Antibiotic Kendomycin by Macrocyclization using Photo-Fries Rearrangement and Ring-Closing Metathesis". Angewandte Chemie International Edition.
  9. (2010). "In Pursuit of a Competitive Target: Total Synthesis of the Antibiotic Kendomycin". Angewandte Chemie International Edition.

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macrolidesantibioticsquinone-methidestotal-synthesis