Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2007 - Issue 1
497
Views
5
CrossRef citations to date
0
Altmetric
Original Articles

Stereoselective Synthesis of Rubrenoic and nor‐Rubrenoic acids

, , , , &
Pages 54-71 | Received 26 Jun 2007, Published online: 25 Jan 2008

REFERENCES

  • Baslow , M. H. 1969 . Marine Pharmacology 8 – 55 . Baltimore, MD : Williams and Wilkins .
  • Holland , G. S. , Jamieson , D. D. , Reichelt , J. L. , Viset , G. and Wells , R. J. 1984 . Three aromatic acids from a marine bacterium . Chem. Ind. , 23 : 850 – 851 .
  • Ritzau , M. , Drautz , H. , Zähner , H. and Zeeck , A. 1993 . Metabolic products of microorganisms, 266: serpentene, a novel polyene carboxylic acid from Streptomyces . Liebigs Ann. Chem. , : 433 – 435 .
  • Wenzel , S. C. and Bode , H. B. 2004 . Novel polyene carboxylic acids from Streptomyces. . J. Nat. Prod. , 67 : 1631 – 1633 .
  • Harper , D. E. and Welch , D. R. 1992 . Isolation, purification, synthesis, and antiinvasive/antimetastatic activity of U‐77863 and U‐77864 from Streptomyces griseoluteus strain WS6714 . J. Antibiot. , 45 : 1827 – 1836 .
  • Gehrt , A. , Erkel , G. , Anke , T. and Sterner , O. 1998 . Cycloepoxydon, 1‐hydroxy‐2‐hydroxymethyl‐3‐pent‐1‐enylbenzene and 1‐hydroxy‐2‐hydroxymethyl‐3‐pent‐1,3‐dieenylbenzene, new inhibitors of eukaryotic signal transduction . J. Antibiot. , 51 : 455 – 463 .
  • Mukku , V. J. R. V. , Maskey , R. P. , Monecke , P. , Grün‐Wollny , I. and Laatsch , H. 2002 . 5‐(2‐Methylphenyl)‐4‐pentenoic acid from a terrestrial Streptomycete . Z. Naturforschung , 57b : 335 – 337 .
  • DeVault , R. L. , Schmitz , H. and Hooper , I. R. 1965 . Demetric acid, a new cytotoxic agent . Antimicrob. Agents Chemother. , 5 : 796 – 800 .
  • Hashimoto , M. , Hayashi , K. , Murai , M. , Fujii , T. , Nishikawa , M. , Kiyoto , S. , Okuhara , M. , Kohsaka , M. and Imanaka , H. 1992 . WS9326A, a novel tachykinin antagonist isolated from Streptomyces violaceusniger no. 9326 . J. Antibiot. , 45 : 1064 – 1070 .
  • Hayashi , K. , Hashimoto , M. , Shigematsu , N. , Nishikawa , M. , Ezaki , M. , Yamashita , M. , Kiyoto , S. , Okuhara , M. , Kohsaka , M. and Imanaka , H. 1992 . WS9326A, a novel tachykinin antagonist isolated from Streptomyces violaceusniger no. 9326: taxonomy, fermentation, isolation, physico‐chemical properties and biological activities . J. Antibiot. , 45 : 1055 – 1063 .
  • Toki , S. , Agatsuma , T. , Ochiai , K. , Saitoh , Y. , Ando , K. , Nakanishi , S. , Lokker , N. A. , Giese , N. A. and Matsuda , Y. 2001 . RP‐1776, a novel cyclic peptide produced by Streptomyces sp., inhibits the binding of PDGF to the extracellular domain of its receptor . J. Antibiot. , 54 : 405 – 414 .
  • Rickards , R. W. 1996 . Annual Report Bio‐organic Chemistry 1 – 9 . Camberra, , Australia : Australian National University .
  • Miyaura , N. and Suzuki , A. 1995 . Palladium‐catalyzed cross‐coupling reactions of organoboron compounds . Chem. Rev. , 95 : 2457 – 2483 .
  • Johnson , C. R. and Braun , M. P. 1993 . A two‐step, three‐component synthesis of PGE1: Utilization of alpha‐iodo enones in Pd(0)‐catalyzed cross‐couplings of organoboranes . J. Am. Chem. Soc. , 115 : 11014 – 11015 .
  • Dorman , D. E. , Jautelat , M. and Roberts , J. D. 1971 . Carbon‐13 nuclear magnetic resonance spectroscopy: quantitative correlations of the carbon chemical shifts of acyclic alkenes . J. Org. Chem. , 36 : 2757 – 2766 .
  • de Haan , J. W. and van de Ven , L. J. M. 1973 . Configurations and conformations in acyclic, unsaturated hydrocarbons: a 13C NMR study . Org. Magn. Resonance , 5 : 147 – 153 .
  • Stork , G. and Zhao , K. 1989 . A stereoselective synthesis of (Z)‐1‐iodo‐1‐alkenes . Tetrahedron Lett. , 30 : 2173 – 2174 .
  • Barchín , B. M. , Valenciano , J. , Cuadro , A. M. , Alvarez‐Builla , J. and Vaquero , J. J. 1999 . Use of the Stille coupling reaction on heteroaromatic cations: synthesis of substituted quinolizinium salts . Org. Lett. , 1 : 545 – 548 .
  • White , J. D. , Blakemore , P. R. , Browder , C. C. , Hong , J. , Lincoln , C. M. , Nagornyy , P. A. , Robarge , L. A. and Wardrop , D. J. 2001 . Total synthesis of the marine toxin polycavernoside A via selective macrolactonization of a trihydroxy carboxylic acid . J. Am. Chem. Soc. , 123 : 8593 – 8595 .

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.