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Application of the de Mayo reaction to the preparation of tricyclo[6.3.0.02,6]undecanes: a photochemical synthesis of (.+-.)-hirsutene

Cite this: J. Org. Chem. 1987, 52, 13, 2905–2910
Publication Date (Print):June 1, 1987
https://doi.org/10.1021/jo00389a046
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    Cited By

    This article is cited by 38 publications.

    1. Riley M. Kelch, Andrew Whyte, Eunji Lee, Tehshik P. Yoon. Investigating the Effect of Lewis Acid Co-catalysts on Photosensitized Visible-Light De Mayo Reactions. Organic Letters 2023, 25 (22) , 4098-4102. https://doi.org/10.1021/acs.orglett.3c01321
    2. Markus D. Kärkäs, John A. Porco, Jr., and Corey R. J. Stephenson . Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis. Chemical Reviews 2016, 116 (17) , 9683-9747. https://doi.org/10.1021/acs.chemrev.5b00760
    3. Goverdhan Mehta, , A. Srikrishna. Synthesis of Polyquinane Natural Products:  An Update. Chemical Reviews 1997, 97 (3) , 671-720. https://doi.org/10.1021/cr9403650
    4. Giulio Goti, Kavyasree Manal, Jayaraman Sivaguru, Luca Dell’Amico. The impact of UV light on synthetic photochemistry and photocatalysis. Nature Chemistry 2024, 28 https://doi.org/10.1038/s41557-024-01472-6
    5. Noelia Salaverri, José Alemán, Leyre Marzo. Harnessing the Power of the De Mayo Reaction: Unveiling a Photochemical and Photocatalytic Masked [2+2] Methodology for Organic Synthesis. Advanced Synthesis & Catalysis 2024, 366 (2) , 156-167. https://doi.org/10.1002/adsc.202300647
    6. Norbert Hoffmann. Photochemical Synthesis of Fine Chemicals. 2024https://doi.org/10.1016/B978-0-443-15742-4.00013-2
    7. Wenzhao Zhang, Sanzhong Luo. Visible-light promoted de Mayo reaction by zirconium catalysis. Chemical Communications 2022, 58 (93) , 12979-12982. https://doi.org/10.1039/D2CC05029C
    8. Anthony Bongso, Robby Roswanda, Yana Maolana Syah. Recent advances of carbonyl olefination via McMurry coupling reaction. RSC Advances 2022, 12 (25) , 15885-15909. https://doi.org/10.1039/D2RA00724J
    9. Monosij Nandy, Swagata Das, Samik Nanda. Cyclobutane based “overbred intermediates” and their exploration in organic synthesis. Organic & Biomolecular Chemistry 2022, 20 (8) , 1582-1622. https://doi.org/10.1039/D1OB02361F
    10. Tiffany O. Paulisch, Lukas A. Mai, Felix Strieth‐Kalthoff, Michael J. James, Christian Henkel, Dirk M. Guldi, Frank Glorius. Dynamische kinetische Sensibilisierung von β‐Dicarbonyl‐verbindungen – Zugang zu mittelgroßen Ringen durch eine De‐Mayo‐artige Ringerweiterung. Angewandte Chemie 2022, 134 (5) https://doi.org/10.1002/ange.202112695
    11. Tiffany O. Paulisch, Lukas A. Mai, Felix Strieth‐Kalthoff, Michael J. James, Christian Henkel, Dirk M. Guldi, Frank Glorius. Dynamic Kinetic Sensitization of β‐Dicarbonyl Compounds—Access to Medium‐Sized Rings by De Mayo‐Type Ring Expansion. Angewandte Chemie International Edition 2022, 61 (5) https://doi.org/10.1002/anie.202112695
    12. Debayan Sarkar, Nabakumar Bera, Subrata Ghosh. [2+2] Photochemical Cycloaddition in Organic Synthesis. European Journal of Organic Chemistry 2020, 2020 (10) , 1310-1326. https://doi.org/10.1002/ejoc.201901143
    13. Richard C. Larock, Gilson Zeni. Formation of Alkenes by Elimination. 2018, 1-74. https://doi.org/10.1002/9781118662083.cot02-002
    14. Richard C. Larock, Anton V. Dubrovskiy, Nataliya A. Markina. Formation of Aldehydes and Ketones by Cyclization and Annulation Reactions. 2018, 1-61. https://doi.org/10.1002/9781118662083.cot08-006
    15. Jie Jack Li. de Mayo reaction. 2014, 200-201. https://doi.org/10.1007/978-3-319-03979-4_84
    16. Takeshi Takeda, Akira Tsubouchi. The McMurry Coupling and Related Reactions. 2013, 1-470. https://doi.org/10.1002/0471264180.or082.01
    17. . de Mayo Reaction. 2010, 858-861. https://doi.org/10.1002/9780470638859.conrr183
    18. . Large‐Ring Carbocycles. 2010, 423-588. https://doi.org/10.1002/9780470872215.ch5
    19. Jie Jack Li. de Mayo reaction. 2009, 173-174. https://doi.org/10.1007/978-3-642-01053-8_76
    20. Alan C Weedon, John S Morrison. The photochemistry of trans -isohumulone, a bitter flavouring component of beer. Canadian Journal of Chemistry 2008, 86 (8) , 791-798. https://doi.org/10.1139/v08-072
    21. Jone Iriondo‐Alberdi, Michael F. Greaney. Photocycloaddition in Natural Product Synthesis. European Journal of Organic Chemistry 2007, 2007 (29) , 4801-4815. https://doi.org/10.1002/ejoc.200700239
    22. Jie Jack Li. De Mayo reaction. 2003, 105-106. https://doi.org/10.1007/978-3-662-05336-2_83
    23. Jie Jack Li. de Mayo reaction. 2002, 93-94. https://doi.org/10.1007/978-3-662-04835-1_78
    24. Thomas Lectka. The McMurry Reaction. 1995, 85-131. https://doi.org/10.1002/9783527615179.ch03
    25. Christopher M. Rayner. One or More CC Bond(s) Formed by Condensation: Condensation of Nonheteroatom Linked Functions, Halides, Chalcogen or Nitrogen Functions. 1995, 673-717. https://doi.org/10.1016/B0-08-044705-8/00282-X
    26. . References to Volume 1. 1995, 1147-1316. https://doi.org/10.1016/B0-08-044705-8/09009-9
    27. Wolfgang Oppolzer, Chantal Robyr. Synthesis of (±)-hirsutene by a catalytic allylpalladium-alkyne cyclization/carbonylation cascade. Tetrahedron 1994, 50 (2) , 415-424. https://doi.org/10.1016/S0040-4020(01)80764-X
    28. T.K. Sarkar, S.K. Gosh, P.S.V. Subba Rao, T.K. Satapathi, V.R. Mamdapur. Cyclopentanoid allylsilanes in synthesis of di- and triquinanes. A stereoselective synthesis of (±)-hirsutene. Tetrahedron 1992, 48 (33) , 6897-6908. https://doi.org/10.1016/S0040-4020(01)89880-X
    29. Leo A. Paquette, Kevin J. Moriarty, Chien‐Chang Shen. Sequential Annulation in Molecular Construction. A Short, Stereocontrolled Synthesis of (±)‐Hirsutene. Israel Journal of Chemistry 1991, 31 (3) , 195-198. https://doi.org/10.1002/ijch.199100022
    30. J. D. Connolly, R. A. Hill. Sesquiterpenoids. 1991, 153-653. https://doi.org/10.1007/978-1-4899-4513-6_3
    31. Graeme M. Robertson. Pinacol Coupling Reactions. 1991, 563-611. https://doi.org/10.1016/B978-0-08-052349-1.00073-1
    32. Alan C. Weedon. Photochemical reactions involving enols. 1990, 591-638. https://doi.org/10.1002/9780470772294.ch9
    33. T.K. Sarkar, S.K. Ghosh, P.S.V. Subba Rao, V.R. Mamdapur. Cyclopentanoid allylsilanes in synthesis : A stereoselective synthesis of ()-hirsutene. Tetrahedron Letters 1990, 31 (24) , 3465-3466. https://doi.org/10.1016/S0040-4039(00)97423-9
    34. Brindaban C. Ranu, Dipak C. Sarkar, Manas K. Basu. A simple and efficient route towards usefully functionalised six and seven-membered ring systems via α-hydroxycyclobutane rearrangement followed by retroaldol cleavage. Tetrahedron 1989, 45 (10) , 3107-3114. https://doi.org/10.1016/S0040-4020(01)80137-X
    35. B. W. DISANAYAKA, A. C. WEEDON. ChemInform Abstract: Application of the de Mayo Reaction to the Preparation of Tricyclo‐(6.3.0.02,6)undecanes: A Photochemical Synthesis of (.+‐.)‐Hirsutene.. ChemInform 1988, 19 (1) https://doi.org/10.1002/chin.198801147
    36. George Majetich, Jean Defauw. Intramolecular additions of allylsilanes in triquinane synthesis. Studies directed toward the total synthesis of (±)-hirsutene. Tetrahedron 1988, 44 (13) , 3833-3849. https://doi.org/10.1016/S0040-4020(01)86640-0
    37. T. Hudlicky, G. Sinai-Zingde, M.G. Natchus, B.C. Ranu, P. Papadopolous. System oriented design of triquinanes: stereocontrolled synthesis of pentalenic acid and pentalenene. Tetrahedron 1987, 43 (23) , 5685-5721. https://doi.org/10.1016/S0040-4020(01)87747-4
    38. . de Mayo reaction. , 189-190. https://doi.org/10.1007/3-540-30031-7_85

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