Kendomycin

Kendomycin[1]
Names
IUPAC name
(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
Systematic IUPAC name
(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
Other names
(-)-TAN 2162
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
MeSH C485395
PubChem CID
InChI
  • InChI=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 ☒N
    Key: HKLDUJXJTQJSEJ-OLXNOMCWSA-N ☒N
  • 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
    Key: HKLDUJXJTQJSEJ-OLXNOMCWBE
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
Properties
Chemical formula
 C29H42O6
Molar mass 486.64 g/mol
Appearance Yellow powder
Solubility in DMSO, methanol Soluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Kendomycin is an anticancer macrolide first isolated from Streptomyces violaceoruber.[2] It has potent activity as an endothelin receptor antagonist and anti-osteoporosis agent.[3] It also has strong cytotoxicity against various tumor cell lines.[2]

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.[4] The total number of syntheses stands at 6.[5][6][7][8][9]

References

  1. ↑ Kendomycin Archived 2008-05-16 at the Wayback Machine at Alexis-Biochemicals
  2. 1 2 H B Bode; A Zeeck (2000). "Structure and biosynthesis of kendomycin, a carbocyclic ansa-compound from Streptomyces". J. Chem. Soc. Perkin Trans. 1. 323 (3): 323–328. doi:10.1039/a908387a.
  3. ↑ Burke Research Group Archived 2006-08-29 at the Wayback Machine University of Wisconsin
  4. ↑ Yu Yuan; Hongbin Men; Chulbom Lee (2004). "Total Synthesis of Kendomycin: A Macro−C−Glycosidation Approach". J. Am. Chem. Soc. 126 (45): 14720–14721. doi:10.1021/ja0447154. PMC 1785127. PMID 15535687.
  5. ↑ A B Smith III; E F Mesaros; E Meyer (2006). "Evolution of a Total Synthesis of (−)-Kendomycin Exploiting a Petasis−Ferrier Rearrangement/Ring-Closing Olefin Metathesis Strategy". J. Am. Chem. Soc. 128 (15): 5292–9. doi:10.1021/ja060369+. PMID 16608366.
  6. ↑ J T Lowe; J S Panek (2008). "Total Synthesis of (−)-Kendomycin". Org. Lett. 10 (17): 3813–6. doi:10.1021/ol801499s. PMID 18698784.
  7. ↑ K B Bahnck; S D Rychnovsky (2008). "Formal Synthesis of (−)-Kendomycin Featuring a Prins-Cyclization to Construct the Macrocycle". J. Am. Chem. Soc. 130 (13): 13177–81. doi:10.1021/ja805187p. PMC 2697922. PMID 18767844.
  8. ↑ Magauer, Thomas; Martin, Harry J.; Mulzer, Johann (2009). "Total Synthesis of the Antibiotic Kendomycin by Macrocyclization using Photo-Fries Rearrangement and Ring-Closing Metathesis". Angewandte Chemie International Edition. 48 (33): 6032–6. doi:10.1002/anie.200900522. PMID 19350596.
  9. ↑ Martin, Harry J.; Magauer, Thomas; Mulzer, Johann (2010). "In Pursuit of a Competitive Target: Total Synthesis of the Antibiotic Kendomycin". Angewandte Chemie International Edition. 49 (33): 5614–26. doi:10.1002/anie.201000227. PMID 20818753.
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