{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 387363125 | Reference=<ref>[http://www.alexis-biochemicals.com/Kendomycin.5+M5acc5c8c65d.0.html Kendomycin] {{Webarchive|url=https://web.archive.org/web/20080516164958/http://www.alexis-biochemicals.com/Kendomycin.5+M5acc5c8c65d.0.html |date=2008-05-16 }} at Alexis-Biochemicals</ref> | 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[17.3.1.1<sup>6,9</sup>.0<sup>2,7</sup>]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[17.3.1.1<sup>6,9</sup>.0<sup>2,7</sup>]tetracosa-2,5,7,14-tetraen-4-one | OtherNames=(-)-TAN 2162 |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo=59785-91-0 | PubChem=5472093 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 523927 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 4582118 | SMILES = C[C@H]\1CC[C@@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)C3=C(C(=O)C(=C4C3=C[C@@](O4)([C@H](C[C@@H](C/C(=C1)/C)C)C)O)C)O)C)O)C | 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 = {{stdinchicite|changed|chemspider}} | 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 = {{stdinchicite|changed|chemspider}} | StdInChIKey = HKLDUJXJTQJSEJ-OLXNOMCWSA-N | RTECS = | MeSHName = C485395 }} |Section2={{Chembox Properties | Formula=C<sub>29</sub>H<sub>42</sub>O<sub>6</sub> | 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''.<ref name = "Bode">{{cite journal |author1=H B Bode |author2=A Zeeck | journal = J. Chem. Soc. Perkin Trans. 1 | year = 2000 | volume = 323 | doi = 10.1039/a908387a | title = Structure and biosynthesis of kendomycin, a carbocyclic ansa-compound from Streptomyces | pages = 323–328 | issue = 3}}</ref> It has potent activity as an endothelin receptor antagonist and anti-osteoporosis agent.<ref>[http://www.chem.wisc.edu/~burke/Kendo.htm Burke Research Group] {{Webarchive|url=https://web.archive.org/web/20060829132137/http://www.chem.wisc.edu/~burke/Kendo.htm |date=2006-08-29 }} University of Wisconsin</ref> It also has strong cytotoxicity against various tumor cell lines.<ref name="Bode"/>
==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.<ref>{{cite journal |author1=Yu Yuan |author2=Hongbin Men |author3=Chulbom Lee | journal = J. Am. Chem. Soc. | year = 2004 | volume = 126 | pages = 14720–14721 | doi = 10.1021/ja0447154 | title = Total Synthesis of Kendomycin: A Macro−C−Glycosidation Approach | pmid = 15535687 | issue = 45 | pmc = 1785127}}</ref> The total number of syntheses stands at 6.<ref>{{cite journal |author1=A B Smith III |author2=E F Mesaros |author3=E Meyer | journal = J. Am. Chem. Soc. | year = 2006 | volume = 128 | pages = 5292–9 | doi = 10.1021/ja060369+| title = Evolution of a Total Synthesis of (−)-Kendomycin Exploiting a Petasis−Ferrier Rearrangement/Ring-Closing Olefin Metathesis Strategy | pmid = 16608366 | issue = 15}}</ref><ref>{{cite journal |author1=J T Lowe |author2=J S Panek | journal = Org. Lett. | year = 2008 | volume = 10 | pages = 3813–6 | doi = 10.1021/ol801499s | title = Total Synthesis of (−)-Kendomycin | pmid = 18698784 | issue = 17}}</ref><ref>{{cite journal |author1=K B Bahnck |author2=S D Rychnovsky | journal = J. Am. Chem. Soc. | year = 2008 | volume = 130 | pmid = 18767844 | issue = 13 | pmc = 2697922 | pages = 13177–81 | doi=10.1021/ja805187p | title = Formal Synthesis of (−)-Kendomycin Featuring a Prins-Cyclization to Construct the Macrocycle}}</ref><ref>{{cite journal|doi = 10.1002/anie.200900522|pmid = 19350596|title = Total Synthesis of the Antibiotic Kendomycin by Macrocyclization using Photo-Fries Rearrangement and Ring-Closing Metathesis|year = 2009|last1 = Magauer|first1 = Thomas|last2 = Martin|first2 = Harry J.|last3 = Mulzer|first3 = Johann|journal = Angewandte Chemie International Edition|volume = 48|issue = 33|pages = 6032–6|doi-access = free}}</ref><ref>{{cite journal|doi=10.1002/anie.201000227|pmid=20818753|title=In Pursuit of a Competitive Target: Total Synthesis of the Antibiotic Kendomycin|year=2010|last1=Martin|first1=Harry J.|last2=Magauer|first2=Thomas|last3=Mulzer|first3=Johann|journal=Angewandte Chemie International Edition|volume=49|issue=33|pages=5614–26}}</ref>
==References== {{reflist}}
Category:Macrolides Category:Antibiotics Category:Quinone methides Category:Total synthesis