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Synthesis and biological evaluation of a monocyclic, fully functional analog of compactin
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    Synthesis and biological evaluation of a monocyclic, fully functional analog of compactin
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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 1989, 32, 1, 197–202
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    https://doi.org/10.1021/jm00121a036
    Published January 1, 1989

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    This article is cited by 34 publications.

    1. Jens M. J. Nolsøe, Simen Antonsen, Carl H. Görbitz, Trond V. Hansen, Jannicke I. Nesman, Åsmund K. Røhr, Yngve H. Stenstrøm. Total Synthesis of (−)-Mucosin and Revision of Structure. The Journal of Organic Chemistry 2018, 83 (24) , 15066-15076. https://doi.org/10.1021/acs.joc.8b02318
    2. Heiko Oertling,, Aurélia Reckziegel,, Horst Surburg, and, Heinz-Juergen Bertram. Applications of Menthol in Synthetic Chemistry. Chemical Reviews 2007, 107 (5) , 2136-2164. https://doi.org/10.1021/cr068409f
    3. Andrew D. Gribble,, Roland E. Dolle,, Antony Shaw,, David McNair,, Riccardo Novelli,, Christine E. Novelli,, Brian P. Slingsby,, Virendra P. Shah,, David Tew,, Barbara A. Saxty,, Mark Allen,, Pieter H. Groot,, Nigel Pearce, and, John Yates. ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. Design and Synthesis of 2-Substituted Butanedioic Acids as Novel, Potent Inhibitors of the Enzyme. Journal of Medicinal Chemistry 1996, 39 (18) , 3569-3584. https://doi.org/10.1021/jm960167w
    4. Anthony G. M. Barrett,, Mark L. Boys, and, Terri L. Boehm. Total Synthesis of (+)-Papuamine:  An Antifungal Pentacyclic Alkaloid from a Marine Sponge, Haliclona sp.. The Journal of Organic Chemistry 1996, 61 (2) , 685-699. https://doi.org/10.1021/jo951413z
    5. Todd S. McDermott,, Andrew A. Mortlock, and, Clayton H. Heathcock. Total Syntheses of (−)-Papuamine and (−)-Haliclonadiamine. The Journal of Organic Chemistry 1996, 61 (2) , 700-709. https://doi.org/10.1021/jo951647i
    6. Åsa Rosenquist and, Ingemar Kvarnström, , Björn Classon and, Bertil Samuelsson. Synthesis of Enantiomerically Pure Bis(hydroxymethyl)-Branched Cyclohexenyl and Cyclohexyl Purines as Potential Inhibitors of HIV. The Journal of Organic Chemistry 1996, 61 (18) , 6282-6288. https://doi.org/10.1021/jo9603542
    7. Jens M. J. Nolsøe, Jarl Underhaug, Åshild Moi Sørskar, Simen Gjelseth Antonsen, Karl E. Malterud, Osman Gani, Qiong Fan, Marit Hjorth, Thomas Sæther, Trond V. Hansen, Yngve H. Stenstrøm. Biological Evaluations, NMR Analyses, Molecular Modeling Studies, and Overview of the Synthesis of the Marine Natural Product (−)-Mucosin. Molecules 2024, 29 (5) , 994. https://doi.org/10.3390/molecules29050994
    8. Lais S. D. Azevedo, Anderson R. Aguillon, Marcelo T. Lima, Raquel A. C. Leão, Rodrigo O. M. A. de Souza. Continuous flow synthesis of the lamivudine precursor L-Menthyl Glyoxylate. Journal of Flow Chemistry 2022, 12 (1) , 59-69. https://doi.org/10.1007/s41981-021-00189-8
    9. Haruhiko Fuwa. Synthesis-Driven Stereochemical Assignment of Marine Polycyclic Ether Natural Products. Marine Drugs 2021, 19 (5) , 257. https://doi.org/10.3390/md19050257
    10. Anna Piątek, Christian Chapuis. Diels‐Alder Reaction of Cyclopenta‐1,3‐diene and Anthracene to bis‐Fumarates Derived from Menthol Analogues. ChemistrySelect 2019, 4 (8) , 2288-2292. https://doi.org/10.1002/slct.201803003
    11. Ravindra D. Gaikwad, Monica D. Rane, Sujata V. Bhat. Asymmetric synthesis of (6R)-4-hydroxy-6-substituted-δ-lactones. Tetrahedron: Asymmetry 2017, 28 (1) , 181-185. https://doi.org/10.1016/j.tetasy.2016.12.006
    12. D. Chandra Rao, D. Kumar Reddy, B. Chinnababu, V. Shekhar, Y. Venkateswarlu. Concise Stereoselective Total Synthesis of (4 R , 6 R )-Lactone Moiety Analog of Mevinoline and Compactin. Synthetic Communications 2013, 43 (22) , 2980-2984. https://doi.org/10.1080/00397911.2012.754470
    13. Thummalapally Srikanth Reddy, Dorigondla Kumar Reddy, Manchala Narasimhulu, Dasari Ramesh, Yenamandra Venkateswarlu. Total Synthesis of a Mevinic Acid Analog. Helvetica Chimica Acta 2010, 93 (11) , 2158-2163. https://doi.org/10.1002/hlca.201000062
    14. Deborah A Longbottom, Angus J Morrison, Darren J Dixon, Steven V Ley. Total synthesis of the polyenoyltetramic acid polycephalin C. Tetrahedron 2003, 59 (35) , 6955-6966. https://doi.org/10.1016/S0040-4020(03)00816-0
    15. R. Yoshioka, K. Soga, K. Wakabayashi, G. Takeba, T. Hoson. Hypergravity-induced changes in gene expression in Arabidopsis hypocotyls. Advances in Space Research 2003, 31 (10) , 2187-2193. https://doi.org/10.1016/S0273-1177(03)00243-6
    16. . The Carboxyphosphonates. 2003https://doi.org/10.1201/9780203503676.ch8
    17. K. Krohn. Asymmetric Induction in Diels‐Alder Reactions. 2003, 54-65. https://doi.org/10.1002/9783527620784.ch9
    18. Roman Lenz, Steven V Ley, Dafydd R Owen, Stuart L Warriner. Stereoelectronic effects in the reactions of conformationally restricted, substituted cyclohexane-1,2-diones with 1,2-diols. Tetrahedron: Asymmetry 1998, 9 (14) , 2471-2480. https://doi.org/10.1016/S0957-4166(98)00227-4
    19. James M. Takacs, David A. Quincy, William Shay, Brian E. Jones, Charles R. Ross. Enantioselective Diels-Alder reactions: novel constrained bis(oxazoline) ligand-metal triflate catalysts. Tetrahedron: Asymmetry 1997, 8 (18) , 3079-3087. https://doi.org/10.1016/S0957-4166(97)00323-6
    20. Siméon Arseniyadis, Rosemeire Brondi-Alves, Dmitry V. Yashunsky, Pierre Potier, Loïc Toupet. Formal total synthesis of an A-seco mevinic acid. Tetrahedron 1997, 53 (3) , 1003-1014. https://doi.org/10.1016/S0040-4020(96)01000-9
    21. Taro Nonomura, Makoto Sasaki, Nobuaki Matsumori, Michio Murata, Kazuo Tachibana, Takeshi Yasumoto. Die Struktur von Maitotoxin – II: Konfiguration der C135‐C142‐Seitenkette und absolute Konfiguration des gesamten Moleküls. Angewandte Chemie 1996, 108 (15) , 1786-1789. https://doi.org/10.1002/ange.19961081512
    22. Taro Nonomura, Makoto Sasaki, Nobuaki Matsumori, Michio Murata, Kazuo Tachibana, Takeshi Yasumoto. The Complete Structure of Maitotoxin, Part II: Configuration of the C135C142 Side Chain and Absolute Configuration of the Entire Molecule. Angewandte Chemie International Edition in English 1996, 35 (15) , 1675-1678. https://doi.org/10.1002/anie.199616751
    23. Veejendra K. Yadav, Kamal K. Kapoor. 1,8-diazabicyclo [5.4.0] undec-7-ene: A remarkable base in the epoxidation of α, β-unsaturated-δ-lactones and other enones with anhydrous t-BuOOH. Tetrahedron 1995, 51 (31) , 8573-8584. https://doi.org/10.1016/0040-4020(95)00472-K
    24. S. Arseniyadis, R. Brondi-Alves, Q. Wang, D.V. Yashunsky, P. Potier. An efficient route to the formal total synthesis of A-seco mevinic acid analogues. Tetrahedron Letters 1994, 35 (43) , 7949-7952. https://doi.org/10.1016/0040-4039(94)80019-7
    25. Yurngdong Jahng, Jin-Il Kim. Aza-analogue of mevinolin: Synthesis of substituted octahydroisoquinoline, the bottom half of aza-analogue of mevinolin. Archives of Pharmacal Research 1994, 17 (2) , 104-108. https://doi.org/10.1007/BF02974232
    26. Mikhail S. Ermolenko, Alain Olesker, Gabor Lukacs. Stereoselective synthesis of the tetrasubstituted cyclohexane core of a monocyclic mevinic acid analogue. Tetrahedron Letters 1994, 35 (5) , 711-714. https://doi.org/10.1016/S0040-4039(00)75797-2
    27. Y. Chapleur. The Chemistry and Total Synthesis of Mevinolin and Related Compounds. 1993, 829-937. https://doi.org/10.1007/978-3-642-78250-3_17
    28. A.P. Kozikowski, V.I. Ognyanov, C. Chen, P. Kurian, F.T. Crews. Synthesis and binding studies of an optically pure hexadeoxy-1,4,5-tris(methylenesulfonic acid) analogue of IP3. Tetrahedron Letters 1993, 34 (2) , 219-222. https://doi.org/10.1016/S0040-4039(00)60551-8
    29. Elisabeth A. Bone, Emer M. Cunningham, Alan H. Davidson, W.Alan Galloway, Christopher N. Lewis, Elizabeth M. Morrice, Maxwell M. Reeve, Richard S. Todd, Ingrid M. White. The design and biological evaluation of a series of 3-hydroxy-3-methylglutaryl coenzyme a (HMG-CoA) reductase inhibitors related to dihydromevinolin.. Bioorganic & Medicinal Chemistry Letters 1992, 2 (3) , 223-228. https://doi.org/10.1016/S0960-894X(01)81069-6
    30. Donald S. Karanewsky. Synthetic transformations of the mevinic acid nucleus: Preparation of a monocyclic analogue of compactin. Tetrahedron Letters 1991, 32 (32) , 3911-3914. https://doi.org/10.1016/0040-4039(91)80587-V
    31. Dinesh V. Patel, Eric M. Gordon. C-2 desmethyl seco-mevinic acids. Monocyclic HMG-CoA reductase inbibitors. Bioorganic & Medicinal Chemistry Letters 1991, 1 (10) , 509-512. https://doi.org/10.1016/S0960-894X(01)80455-8
    32. . Asymmetric Induction in Diels‐Alder Reactions. 1990, 54-65. https://doi.org/10.1002/9783527621385.ch9
    33. Pascal Boquel, Yves Chapleur. A new strategy for the synthesis of mevinic acid analogues. Tetrahedron Letters 1990, 31 (13) , 1869-1872. https://doi.org/10.1016/S0040-4039(00)98807-5
    34. Bruce D. Roth, Drago R. Sliskovic, Bharat K. Trivedi. Chapter 16. Treatment of Hypercholesterolemia. 1989, 147-156. https://doi.org/10.1016/S0065-7743(08)60538-2

    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 1989, 32, 1, 197–202
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jm00121a036
    Published January 1, 1989

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