ACS Publications. Most Trusted. Most Cited. Most Read
My Activity

Figure 1Loading Img

Rotenoids. XX.1 Total Synthesis of Rotenone

Cite this: J. Am. Chem. Soc. 1965, 87, 17, 3958–3962
Publication Date (Print):September 1, 1965
    ACS Legacy Archive

    Article Views





    Other access options

    Note: In lieu of an abstract, this is the article's first page.

    Free first page

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.


    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Cited By

    This article is cited by 43 publications.

    1. Saima Perveen, Shuang Yang, Miao Meng, Weici Xu, Guoxiang Zhang, Xinqiang Fang. Asymmetric total synthesis of rotenoids via organocatalyzed dynamic kinetic resolution. Communications Chemistry 2019, 2 (1)
    2. Paulo Marcos Donate, Daniel Frederico. Synthesis of New Agrochemicals. 2019, 223-273.
    3. Andrei Hent, John Andraos. Solutions 251 – 300. 2019, 721-863.
    4. Richard C. Larock, Roman Rozhkov. Inverconversion of Nitriles, Carboxylic Acids, and Derivatives. 2018, 1-81.
    5. Kathy Hadje Georgiou, Stephen C. Pelly, Charles B. de Koning. The first stereoselective synthesis of the natural product, rotenone. Tetrahedron 2017, 73 (7) , 853-858.
    6. Vernic Jackson-Lewis, Deranda Lester, Elena Kozina, Serge Przedborski, Richard J. Smeyne. From Man to Mouse. 2015, 287-306.
    7. Nicole Jung, Franziska Gläser, Stefan Bräse. Synthetic approaches to polycyclic semiochemicals and their derivatives: combinatorial methods towards phytochemicals. Phytochemistry Reviews 2013, 12 (4) , 603-651.
    8. N. R. Krishnaswamy, C. N. Sundaresan. Fascinating organic molecules from nature. Resonance 2013, 18 (5) , 428-439.
    9. Tse‐Lok Ho, Mary Fieser, Louis Fieser. Oxalyl Chloride. 2013, 329-329.
    10. Tse‐Lok Ho, Mary Fieser, Louis Fieser. Oxalyl Chloride. 2013, 329-329.
    11. Tse‐Lok Ho, Mary Fieser, Louis Fieser. Oxalyl Chloride. 2011, 396-397.
    12. José Garcia, Sofia Barluenga, Kristin Beebe, Len Neckers, Nicolas Winssinger. Concise Modular Asymmetric Synthesis of Deguelin, Tephrosin and Investigation into Their Mode of Action. Chemistry – A European Journal 2010, 16 (32) , 9767-9771.
    13. Tse‐Lok Ho, Mary Fieser, Louis Fieser. Oxalyl chloride. 2009, 000-000.
    14. Fang‐Li Zhang, W. Bernd Schweizer, Ming Xu, Andrea Vasella. A New Synthesis of Pteridines Substituted with Branched and Linear Alkenyl Groups at C(6). The Nitroso‐Ene Reaction of 4‐(Alkenoylamino)‐5‐nitrosopyrimidines. Helvetica Chimica Acta 2007, 90 (3) , 521-534.
    15. Tse‐Lok Ho, Mary Fieser, Louis Fieser. Oxalyl chloride. 2006
    16. Kyumin Whang, Jonathan McDonald, Ambereen Khan, Neera Satsangi. A novel osteotropic biomaterial OG‐PLG: Synthesis and in vitro release. Journal of Biomedical Materials Research Part A 2005, 74A (2) , 237-246.
    17. E. David Morgan, Ian D. Wilson. Insect Hormones and Insect Chemical Ecology. 1999, 263-375.
    18. Pinmanee Boontheung, Patrick Perlmutter. A highly-efficient synthesis of benzoxazine-2,4-diones. Tetrahedron Letters 1998, 39 (17) , 2629-2630.
    19. Christopher D. Gabbutt, John D. Hepworth, B. Mark Heron, Jean-Luc Thomas. The oxidative ring expansion of spiro-annulated chroman-4-ones: Syntheses of the rotenoid core and related benzoxanthones. Tetrahedron Letters 1998, 39 (8) , 881-884.
    20. Gerard M. Boland, Dervilla M. X. Donnelly. Isoflavonoids and related compounds. Natural Product Reports 1998, 15 (3) , 241.
    21. G. Pattenden, J. I. G. Cadogan, S. V. Ley. T. 1997, 220-246.
    22. Jonathan M.J. Williams. Acid Halides. 1995, 1-21.
    23. . References to Volume 5. 1995, 1161-1308.
    24. Dario Pini, Antonella Petri, Carlo Rosini, Piero Salvadori, Raffaello Giorgi, Cristina Di Bugno, Luigi Turbanti, Fabio Marchetti. The absolute stereochemistry at C1 and C2 of cis-(+)-2-hydroxy-2-phenylcyclohexanecarboxylic acid (cicloxilic acid). Tetrahedron 1994, 50 (1) , 205-216.
    25. Om V. Singh, Randhir S. Kapil, Chandra P. Garg, Ram P. Kapoor. Oxidative rearrangement of 2-spirochromanones: a novel route for the synthesis of tetrahydroxanthones. Tetrahedron Letters 1991, 32 (40) , 5619-5620.
    26. Masao Tokuda, Hirotake Fujita, Hiroshi Suginome. New facile synthesis of substituted 2-benzylidene-pyrrolidines by the anionic cyclization of δ-alkynylamines. Tetrahedron Letters 1990, 31 (37) , 5353-5356.
    27. . 1. Anti-insect agents. 1988, 21-239.
    28. Guy Cordonnier, Henri Sliwa. A new route to 6‐azachromones. An improved synthesis of 2‐azaxanthone. Journal of Heterocyclic Chemistry 1987, 24 (1) , 111-115.
    29. Mario Gosálvez. Carcinogenesis with the insecticide rotenone. Life Sciences 1983, 32 (8) , 809-816.
    30. Dale L. Boger, Michael D. Mullican. Inverse electron demand diels-alder reactions of 3-carbomethoxy-2-pyrones. Controlled introduction of oxygenated aromatics: benzene, phenol, catechol, resorcinol, pyrogallol annulation.. Tetrahedron Letters 1983, 24 (45) , 4939-4942.
    31. R. Verné, N. De Kimpe, L. De Buyck, W. Steurbaut, M. Sadones, R. Willaert, J. ‐P. Verbeek, N. Schamp. Preparation of synthetic rotenoids (1). Bulletin des Sociétés Chimiques Belges 1980, 89 (6) , 459-485.
    32. I. M. Lockhart. 3‐Chromanones. 1977, 193-206.
    33. Detlef Geffken, Gerwalt Zinner. Zur Reaktion 2,2‐disubstituierter 3‐Hydroxypropionsäuren mit aliphatischen Carbodiimiden. Chemische Berichte 1975, 108 (12) , 3730-3735.
    34. Willy Friedrichsen. Photoreaktionen des 4,6‐Dimethylbenzofuran‐2,3‐dions. Justus Liebigs Annalen der Chemie 1975, 1975 (9) , 1545-1562.
    35. Detlef Geffken, Gerwalt Zinner. Hydroxylamin‐Derivate, LX. Darstellung von Derivaten der 3‐Hydroxypropiohydroxamsäure unter Anwendung der Carbodiimid‐Methode. Chemische Berichte 1973, 106 (7) , 2246-2254.
    36. Helmut Gross, Gerwalt Zinner. Über die Reaktion 1,3‐disubstituierter 2,2‐Dichlor‐4,5‐imidazolidindione mit sek. Aminen. Chemische Berichte 1973, 106 (7) , 2315-2323.
    37. F. M. Dean. The Total Synthesis of Naturally Occurring Oxygen Ring Compounds. 1973, 467-562.
    38. Martin F. Ansell. Preparation of acyl halides. 1972, 35-68.
    39. G. Zinner, N.‐P. Lüpke, U. Dybowski. Über N‐(mono)‐Hydroxyaminale und ihre Reaktion mit Iso(thio)cyansäureestern. 48. Mitt. über Hydroxylamin‐Derivate. Archiv der Pharmazie 1972, 305 (1) , 64-70.
    40. Maximilian Von Strandtmann, Marvin P. Cohen, John Shavel. Reaction of phenolic mannich bases with enamines. General synthesis of pyran‐containing fused ring systems. Journal of Heterocyclic Chemistry 1970, 7 (6) , 1311-1319.
    41. U. Claussen. Natürlich vorkommende Insektizide. 1970, 87-118.
    42. V. Chandrashekar, M. Krishnamurti, T.R. Seshadri. A new approach to the synthesis of rotenoids. Tetrahedron 1967, 23 (5) , 2505-2511.
    43. . Chromanochromanones (The Rotenoids). 1967, 272-327.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Your Mendeley pairing has expired. Please reconnect