An Efficient Method for the Synthesis of (+)-Cyclozonarone, Isozonarol Δ,^8,9 and Isozonarone Δ^8,9

References

• Faulkner , D.J. 1994 . Marine Natural Products. Nat. Prod. Reports , : 355 – 394 .
   Google Scholar
• 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 .
   Web of Science ®Google Scholar
• Talpir , R. , Rudi , A. , Kashman , Y. , Loya , Y. and Hizi , A. 1994 . Three new sesquiterpene hydroquinones from marine origin . Tetrahedron , 50 : 4179 – 4184 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• 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 . Pharmacology and Toxicology , 79 : 300 – 304 .
   PubMedGoogle Scholar
• Barrero , A.F. , Alvarez-Manzaneda , E.J. and Chahboun , R. 1997 . Enantiospecific synthesis of wiedendiol-b from (−)-sclareol and (+)-cis-abienol . Tetrahedron Lett. , 38 : 8101 – 8104 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• Barrero , A.F. , Alvarez-Manzaneda , E.J , Mar Herrador , M. , Chahboun , R. and Galera , P. 1999 . Synthesis and antitumoral activities of marine ent-chromazonarol and related compounds . Bioorg. Med. Lett. , 9 : 2325 – 2328 .
   PubMed Web of Science ®Google Scholar
• Welch , S.C. and Paskasa Rao , A.S.C. 1977 . Stereoselective total syntheses of (±)-zonarol and (±)-isozonarol . Tetrahedron Lett. , : 505 – 508 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• 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 .
   Google Scholar
• Akita , H. , Nozawa , M. and Shimizu , H. 1998 . Synthesis of decalin type chiral synthons based on enzymatic functionalisation and their application to the synthesis of (−)-ambrox and (+)-zonarol . Tetrahedron: Asym. , 1 : 1789 – 1799 .
   Google Scholar
• Schröder , J. , Magg , Ch. 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 .
   Web of Science ®Google Scholar
• Nakano , T. , Villamizar , J. and Maillo , M.A. 1995 . A new entry to (+)-albicanol and (+)-bicyclofarnesol . J. Chem. Research (S) , : 330 – 331 .
   Google Scholar
• Villamizar , J. 1999 . Facile access to drimane-type sesquiterpene (−)-bicyclofarnesol and (−)-valdiviolide acetate . Rev. Latinoamer. Quim. , 27 : 96 – 100 .
   Google Scholar
• Nakano , T. 1989 . “ Highly efficient synthesis of natural drimanic sesquiterpenes, (+)-Confertifolin, (+)-Isodrimenin, (+)-Euryfuran, and (−)-Warburganal ” . In Studies in Natural Products Chemistry Edited by: Atta-ur-Rahman . Vol. 4 , 403 – 429 . Amsterdam : Elsevier . and refs. cited therein
   Google Scholar
• Kurata , K. , Taniguchi , K. and Suzuki , M. 1996 . Cyclozonarone, a sesquiterpene-substituted benzoquinone derivative from the brown alga Dictyopteris undulata . Phytochemistry , 41 : 749 – 752 .
   Web of Science ®Google Scholar
• Cortés , M. , Valderrama , J.A. , Cuellar , M. , Armstrong , V. and Preite , M. 2001 . Synthesis of (+)-cyclozonarone and the absolute configuration of naturally occurring (−)-cyclozonarone . J. Nat. Prod. , 64 : 348 – 349 .
   PubMed Web of Science ®Google Scholar
• Kursanov , D.N. , Parnes , A.N. and Loim , N.M. 1974 . Applications of ionic hydrogenation to organic synthesis . Synthesis , : 633 – 651 .
   Web of Science ®Google Scholar
• Kawano , H. , Itoh , M. , Katoh , T. and Terashima , S. 1997 . Studies toward the synthesis of popolohuanone E: synthesis of natural (+)-arenarol related to the proposed biogenetic precursor of popolohuanone E . Tetrahedron Lett. , 38 : 7769 – 7772 .
   Web of Science ®Google Scholar
• Kawasaki , M. , Matsuda , F. and Terashima , S. 1988 . Synthetic studies on nogalamycin congeners [2]1, 2 chiral synthesis of the CDEF-Ring system of nogalamycin . Tetrahedron , 44 : 5713 – 5725 .
   Web of Science ®Google Scholar