Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 3
573
Views
17
CrossRef citations to date
0
Altmetric
Original Articles

New Access to Sesquiterpene Hydroquinones: Synthesis of (+)‐ent‐Chromazonarol

, , , , &
Pages 311-320 | Received 28 Jul 2005, Published online: 19 Aug 2006

References

  • Faulkner , D. 1998 . Marine natural products . Nat. Prod. Rep. , : 113 – 158 . Faulkner, D. Marine natural product. Nat. Prod. Rep. 1994, 355–394
  • Fenical , W. , Sims , J. J. , Squatrito , D. , Wing , R. M. and Radlick , P. 1973 . Zonarol and isozonarol, fungitoxic hydroquinones from the brown seaweed Dictyopteris zonarioides . J. Org. Chem. , 38 : 2383 – 2386 .
  • Taniguchi , K. , Yamada , J. , Kurata , K. and Suzuki , M. 1993 . Feeding deterrents from the brown alga Dictyopteris undulata against the abalone Haliotis discus hannai. Nippon Suisan Gakkaishi . 59 : 339 – 343 .
  • Rodriguez , J. , Quiñoa , E. , Riguera , R. , Peters , B. M. , Abrell , L. M. and Crews , P. 1992 . The structures and stereochemistry of cytotoxic sesquiterpene quinones from Dactylospongia elegans . Tetrahedron , 48 : 6667 – 6680 .
  • Talpir , R. , Rudi , A. , Kashman , Y. , Loya , Y. and Hizi , A. 1994 . Three new sesquiterpene hydroquinones from marine origin . Tetrahedron , 50 : 4179 – 4184 .
  • Coval , S. J. , Conover , M. A. , Mierzwa , R. , King , A. , Puar , M. S. , Phife , D. W. , Pai , J.‐K. , Burrier , R. E. , Ahn , H.‐S. , Boykov , G. C. , Patel , M. and Pomponi , S. A. 1995 . Wiedendiol‐A and ‐B, cholesteryl ester transfer protein inhibitors from the marine sponge Xestospongia wiedenmayeri . Bio. Med. Chem. Lett. , 5 : 605 – 610 .
  • Urban , S. and Capon , R. J. 1996 . Deoxyspongiaquinones: New sesquiterpene quinones and hydroquinones from a southern Australian marine sponge Euryspongia sp . Aust. J. Chem. , 49 : 611 – 615 .
  • Belisario , M. A. , Maturo , M. , Avagnale , G. , De Rosa , S. , Scopacasa , F. and De Caterina , M. 1996 . In vitro effect of avarone and avarol, a quinone/hydroquinone couple of marine origin, on platelet aggregation . Pharmacol. Toxicol. , 79 : 300 – 304 .
  • Cimino , G. , De Stefano , S. and Minale , L. 1975 . ent‐Chromazonarol, a chroman‐sesquiterpenoid from the sponge Disidea pallencens . Experientia , 31 : 1117 – 1118 . Note that in these papers the optical rotation of ent‐chromazonarol ent‐1 was not reported; only the optical rotation of phenolic monoactate of ent‐1 is reported ([α]D+39 (c 1, CH3Cl))
  • Fenical , W. and McConnell , O. 1975 . Chromazonarol and isochromazonarol, new chromanols from the brown seaweed Dictyopteris undulata (zonariodes) . Experientia , 31 : 1004 – 1005 .
  • Barrero , A. F. , Alvarez‐Manzaneda , E. J. and Chahboun , R. 1997 . Enantiospecific synthesis of wiedendiol‐B from (−)‐sclareol and (+)‐cis‐albienol . Tetrahedron Lett. , 38 : 8101 – 8104 .
  • Barrero , A. F. , Alvarez‐Manzaneda , E. J. and Chahboun , R. 1998 . Synthesis of wiedendiol‐A and wiedendiol‐B from labdane diterpenes . Tetrahedron , 54 : 5635 – 5650 .
  • Barrero , A. F. , Alvarez‐Manzaneda , E. J. , Mar Herrador , M. , Chahboun , R. and Galera , P. 1999 . Synthesis of antitumoral activities of marine ent‐chromazonarol and related compounds . Bioorg. Med. Lett. , 9 : 2325 – 2328 .
  • Welch , S. C. and Paskasa Rao , A. S. C. 1977 . Stereoselective total synthesis of (±)‐zonarol and (±)‐isozonarol . Tetrahedron Lett. , : 505 – 508 .
  • Welch , S. C. and Paskasa Rao , A. S. C. 1978 . Stereoselective total syntheses of the fungitoxic hydroquinones (±)‐zonarol and (±)‐isozonarol . J. Org. Chem. , 43 : 1957 – 1961 .
  • Mori , K. and Komatsu , M. 1986 . Synthesis and absolute configuration of zonarol, a fungitoxic hydroquinone from the brown seaweed Dictyopteris zonarioides . Bull. Soc. Chim. Belg. , 95 : 771 – 781 .
  • Akita , H. , Nozawa , M. and Shimizu , H. 1998 . Synthesis of decalin type chiral synthons based on enzymatic functionalization and their application to the synthesis of (−)‐ambrox and (+)‐zonarol . Tetrahedron: Asymmetry , 1 : 1789 – 1799 .
  • Schröder , J. , Magg , C. and Seifert , K. 2000 . Total synthesis of the marine sesquiterpene hydroquinones zonarol and isozonarol and the sesquiterpene quinones zonarone and isozonarone . Tetrahedron Lett. , 41 : 5469 – 5473 .
  • Villamizar , J. , Orcajo , A. L. , Fuentes , J. , Tropper , E. and Alonso , R. 2002 . Highly efficient synthesis of optically active sesquiterpene hydroquinone (+)‐zonarol and sesquiterpene quinone (+)‐zonarone . J. Chem. Res., Synop. , : 395 – 397 .
  • Villamizar , J. , Orcajo , A. L. , Fuentes , J. , Tropper , E. and Alonso , R. 2003 . An efficient method for the synthesis of (+)‐cyclozonarone, isozonarol Δ8,9 and isozonarone Δ8,9 . Synth. Commun. , 33 : 1121 – 1129 .
  • Nakano , T. , Villamizar , J. and Maillo , M. A. 1995 . A new entry to (+)‐albicanol and (+)‐bicyclofarnesol . J. Chem. Res., Synop. , : 330 – 331 .
  • Villamizar , J. 1999 . Facile access to drimane‐type sesquiterpene (−)‐bicyclofarnesol and (−)‐valdiviolide acetate . Rev. Latinoamer. Quim. , 27 : 96 – 100 .
  • Villamizar , J. , Fuentes , J. , Salazar , F. , Tropper , E. and Alonso , R. 2003 . Facile access to optically active labdane‐type diterpenes from (+)‐manool. Synthesis of (+)‐coronarin E, (+)‐15,16‐epoxy‐8(17), 13(16), 14‐labdatriene and (+)‐labda‐8(17), 13(Z)‐diene‐l5,16‐diol . J. Nat. Prod. , 66 : 1623 – 1627 .
  • Ohloff , G. , Giersch , W. , Pickenhagen , W. , Furrer , A. and Frei , B. 1985 . Significance of the geminal dimethyl group in the odor principle of ambrox . Helv. Chim. Acta , 68 : 2022 – 2029 .
  • Cambie , R. C. , Clark , G. R. , Goeth , M. E. , Rickard , C. E. F. , Rutledge , P. S. , Ryan , G. R. and Woodgate , P. D. 1989 . Chemistry of the podocarpaceae. LXXIV. The conversion of podocarpic acid into γ‐bicyclohomofarnesals . Aust. J. Chem. , 42 : 497 – 509 .
  • Ley , S. V. , Norman , J. , Griffith , W. and Marsden , S. 1994 . Tetrapropylammonium perruthenate, Pr4N+RuO4 −, TPAP: A catalytic oxidant for organic synthesis . Synthesis , : 639 – 665 .
  • Chauvet , F. , Coste , M. , Martres , P. , Perfetti , P. , Waegell , B. and Zahra , J.‐P. 1996 . Synthesis of nor‐norambracetal . Tetrahedron Lett. , 37 : 3695 – 3696 .

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.