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. ^ a b 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.
Allikas: https://en.wikipedia.org/wiki/Kendomycin
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