Rearrangement of Aryl Geranyl Ethers

REFERENCES

• (a) Perry , N. B. ; Foster , L. M. ; Lorimer , S. D. ; May , B. C. H. ; Weavers , R. T. ; Toyota , M. ; Nakaishi , E. ; Asakawa , Y. J. Isoprenyl phenyl ethers from liverworts of the genus Trichocolea: Cytotoxic acitivity, structural corrections, and synthesis. J. Nat. Prod. 1996, 59, 729–733; (b) Baek , S.-H. ; Perry , N. B. ; Weavers , R. T. ; Tangney , R. S. Geranyl phenyl ethers from the New Zealand liverwort Trichocolea hatcheri . J. Nat. Prod. 1998, 61, 126–129; (c) Baek , S.-H. ; Perry , N. B. ; Weavers , R. T. Synthesis of geranyl phenyl ethers based on the cytotoxic monoterpenoids from the liverwort genus Trichocolea . J. Nat. Prod. 1998, 61, 1143–1145; (d) Skehan , P. ; Williamson , K. ; Giarazzi , R. ; Malspeis , L. ; Camalier , R. ; Grever , M. Proc. Ann. Meet. Am. Assoc. Cancer Res. 1993, 34(4), A 2600 (e) Baek , S.-H. ; Oh , H. J. ; Lim , J. A. ; Chun , H. J. ; Lee , H. O. ; Ahn , J. W. ; Perry , N. B. ; Kim , H. M. Biological activities of methyl-4-. Bull. Korean Chem. Soc. 2004, 25, 195–197.
   PubMed Web of Science ®Google Scholar
• (a) Redfern , R. E. ; McGovern , T. P. ; Sarmiento , R. ; Beroza , M. Juvenile hormone activity of mixed ethers containing a phenyl and a terpenoid moiety applied topically to the large milkweed bug and the yellow mealworm . J. Econ. Entomol. 1971 , 64 , 374 – 376 ; (b) Arnold , Z. ; Kohovcová , J. ; Pánková , M. ; Svoboda , M. ; Tichý , M. ; Šorm , F. Natural and synthetic materials with insect hormone activity, XIV: Synthesis of substituted phenyl geranyl ethers and related compounds . Coll. Czech. Chem. Commun. 1973 , 38 , 261 – 269 ; (c) Kiguchi , K. ; Mori , T. ; Akai , H. Effects of anti-juvenile hormone “ETB” on the development and metamorphosis of the silkworm Bombyx Mori. Appl. Ent. Zool. 1974 , 9 , 29 – 33 ; (d) Hammock , B. D. ; Gill , S. S. ; Casida , J. E. Synthesis and morphogenetic activity of derivatives and analogs of aryl geranyl ether juvenoids . J. Agr. Food Chem. 1974 , 22 , 379 – 385 ; (e) Fujita , N. ; Furuta , K. ; Ashibe , K. ; Yoshida , S. ; Yamada , N. ; Shiotsuki , T. ; Kiucki , M. ; Kuwano , E. Juvenile hormone activity of optically active ethyl 4-(2-benzylalkyloxy)benzoates inducing precocious metamorphosis . J. Pestic. Sci. 2008 , 33 , 383 – 386 ; (f) Vig , O. P. ; Trehan , I. R. ; Kad , G. I. ; Grewai , M. S. Insect juvenile hormone analogs, part III: Synthesis of biologically active geranyl aromatic ethers and derivatives containing cyclopropane and substituted cyclopropane rings . Indian J. Chem. 1979 , 17B , 54 – 56 ; (g) Yamada , Y. ; Nakatani , N. ; Fuwa , H. Spasmolytic activity of geranyloxycoumarin-related compounds . Agric. Biol. Chem. 1987 , 51 , 1711 – 1713 ; (h) Nishiyama , Y. ; Iwase , K. ; Okada , S. ; Takeuchi , S. ; Moriyasu , M. ; Kamigauchi , M. ; Koyama , J. ; Takeuchi , A. ; Tokuda , H. ; Kim , H.-S. ; Wataya , Y. ; Takeda , K. ; Liu , Y.-N. ; Wu , P.-C. ; Sastow , K. ; Akiyama , T. ; Lee , K.-H. Geranyl derivatives of isoquinole alkaloids show increased biological activities . Heterocycles 2010 , 81 , 1193 – 1229 .
   Web of Science ®Google Scholar
• Baraldi , G. P. ; Manfredini , S. ; Simoni , O. ; Tabrizi , M. A. ; Balzarini , J. ; De Clercq , E. Geiparvarin analogs, 3: Synthesis and cytostatic activity of 3(2H)-furanone and 4,5-dihydro-3(2H)-furanone congeners of geiparvarin, containing a geraniol-like fragment in the side chain . J. Med. Chem. 1992 , 35 , 1877 – 1882 .
   PubMed Web of Science ®Google Scholar
• (a) Tőrincsi , M. ; Kolonits , P. ; Pálosi , E. ; Fekete , M. ; Novák , L. Short and efficient method for the preparation of furo[3,2-f]quinoline . Arkivoc 2008 , 3 , 43 – 53 ; (b) Tőrincsi , M. ; Kolonits , P. ; Pálosi , E. ; Novák , L. Synthesis of Furo[3,2-f]isoquinolines by aromatic claisen rearrangement and subsequent cyclization . Synthesis 2007 , 284 – 288 ; and references therein.
   Google Scholar
• Karanewsky , D. S. ; Kishi , Y. New conditions for controlled claisen rearrangements of allyl aryl ethers . J. Org. Chem. 1976 , 41 , 3026 – 3027 .
   Web of Science ®Google Scholar
• Some ethers of isoquinolin-5-ol showed strong bactericidal activity on Helicobacter pylori : Yoshida , Y. ; Barrett , D. ; Azami , H. ; Morinaga , C. ; Matsumoto , S. ; Matsumoto , Y. ; Takasugi , H. Studies on anti–Helicobacter pylori agents, part I: Benzyloxyisoquinoline derivatives . Bioorg. Med. Chem. 1999 , 7 , 2647 – 2650 .
   PubMed Web of Science ®Google Scholar
• (a) The abnormal Claisen rearrangement was first reported by Lauer and Filbert. Lauer , W. M. ; Filbert , W. F. The rearrangement of phenyl allyl ethers. J. Am. Chem. Soc. 1936, 58, 1388–1391; (b) Abnormal Claisen rearrangement is a stepwise process consisting of three consecutive steps: [3,3]-rearrangement, homo[1,5]-H shift, and [1,5]-H migration. Schobert , R. ; Siegfried , S. ; Gordon , G. ; Mulholland , D. ; Nieuwenhuyzen , M. Abnormal claisen rearrangements of tetronates and stereoselective ring opening of intermediate spirocyclopropanes. Tetrahedron Lett. 2001, 42, 4561–4564; (c) Nakamura , S. ; Ishihara , K. ; Yamamoto , H. Lewis acid–assisted chiral Brønsted acids: Abnormal Claisen rearrangements and succesive cyclizations. J. Am. Chem. Soc. 2000, 122, 8131–8140; (d) Meyer , M. P. ; DelMonte , A. J. ; Singleton , D. A. Reinvestigation of the isotope effects for the claisen and aromatic claisen rearrangements: The nature of the claisen transition states. J. Am. Chem. Soc. 1999, 121, 10865–10874; (e) Li , Jizhen ; Mi , Y. ; He , J. Deng , X. A short and efficient synthesis of Licochalcone E. Synlett 2010, 2289–2292; (f) Ito , H. ; Sato , A. ; Taguchi , T. Enantioselective aromatic Claisen rearrangement. Tetrahedron Lett. 1997, 38, 4815–4819; and references cited therein. (g) For recent excellent monographs on the Claisen rearrangement, see The Claisen Rearrangement ; Hersemann , M. ; Nubbemeyer , U. (Eds.); Wiley-VCH Verlag GmbH: New York, 2007; p. 512; (h) Castro , A. M. M. Claisen rearrangement over the past nine decades. Chem. Rev. 2004, 104, 2939–3002; (i) Nubbemeyer , U. Recent advances in asymmetric [3,3]-Sigmatropic rearrangements. Synthesis 2003, 961–1008.
   Google Scholar
• Earlier we observed similar rearrangement in the acid-catalyzed reaction of hydroquinone derivatives and cyclohexan-1,2-diol . Orovecz , O. ; Kovács , P. ; Kolonits , P. ; Párkányi , L. ; Szabó , É. ; Novak , L. Rearrangement of allyl aryl ethers, part V: Reaction of 2,5-dialkoxyhydroquinone with cycloalkanediols . Synthesis 2002 , 2711 – 2716 .
   Web of Science ®Google Scholar