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Total Synthesis of the Hallucinogenic Neoclerodane Diterpenoid Salvinorin A

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    Total Synthesis of the Hallucinogenic Neoclerodane Diterpenoid Salvinorin A
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    Graduate School of Science and Technology, Niigata University, 8050, 2-Nocho, Ikarashi, Nishi-ku, Niigata 950-2181, Japan, and Faculty of Engineering, Niigata University, 8050, 2-Nocho, Ikarashi, Nishi-ku, Niigata 950-2181, Japan
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    Cite this: Org. Lett. 2008, 10, 7, 1365–1368
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    https://doi.org/10.1021/ol800101v
    Published March 1, 2008
    Copyright © 2008 American Chemical Society
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    Abstract

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    Total synthesis of salvinorin A (1), a neoclerodane diterpenoid having the most potent hallucinogenic activity and a selective κ-opioid agonist, was completed in 20 steps starting from enantiomerically pure hydroxy-Wieland−Miescher ketone 5.

    Copyright © 2008 American Chemical Society

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     Graduate School of Science and Technology.

    ‡

     JSPS Research Fellow.

    §

     Faculty of Engineering.

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    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

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    This article is cited by 52 publications.

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    42. Christopher W. Cunningham, Richard B. Rothman, Thomas E. Prisinzano. Neuropharmacology of the Naturally Occurring κ-Opioid Hallucinogen Salvinorin A. Pharmacological Reviews 2011, 63 (2) , 316-347. https://doi.org/10.1124/pr.110.003244
    43. Don Antoine Lanfranchi, Christophe Bour, Gilles Hanquet. Enantioselective Access to Key Intermediates for Salvinorin A and Analogues. European Journal of Organic Chemistry 2011, 2011 (15) , 2818-2826. https://doi.org/10.1002/ejoc.201100207
    44. Hisahiro Hagiwara, Takashi Nojima, Yuhki Suka, Takashi Hoshi, Toshio Suzuki. First Total Synthesis of the Neo-Clerodane Diterpenoid Salvinorin F. Natural Product Communications 2011, 6 (3) https://doi.org/10.1177/1934578X1100600306
    45. James R. Hanson. Natural Products from the Hallucinogenic Sage. Science Progress 2010, 93 (2) , 171-180. https://doi.org/10.3184/003685010X12626983776947
    46. Kimberly M. Lovell, Katherine M. Prevatt-Smith, Anthony Lozama, Thomas E. Prisinzano. Synthesis of Neoclerodane Diterpenes and Their Pharmacological Effects. 2010, 141-185. https://doi.org/10.1007/128_2010_82
    47. Anthony Lozama, Thomas E. Prisinzano. Chemical methods for the synthesis and modification of neoclerodane diterpenes. Bioorganic & Medicinal Chemistry Letters 2009, 19 (18) , 5490-5495. https://doi.org/10.1016/j.bmcl.2009.07.069
    48. Hisahiro Hagiwara, Yuhki Suka, Takashi Nojima, Takashi Hoshi, Toshio Suzuki. Second-generation synthesis of salvinorin A. Tetrahedron 2009, 65 (25) , 4820-4825. https://doi.org/10.1016/j.tet.2009.04.053
    49. Cécile Béguin, Katharine K. Duncan, Thomas A. Munro, Douglas M. Ho, Wei Xu, Lee-Yuan Liu-Chen, William A. Carlezon, Bruce M. Cohen. Modification of the furan ring of salvinorin A: Identification of a selective partial agonist at the kappa opioid receptor. Bioorganic & Medicinal Chemistry 2009, 17 (3) , 1370-1380. https://doi.org/10.1016/j.bmc.2008.12.012
    50. James R. Hanson. Diterpenoids. Natural Product Reports 2009, 26 (9) , 1156. https://doi.org/10.1039/b807311m
    51. Hisahiro Hagiwara, Masato Nozawa. Highly Oxygenated Diterpenoids Associated to the Central Nervous System: Syntheses of Salvinorin and Forskolin. Journal of Synthetic Organic Chemistry, Japan 2009, 67 (11) , 1115-1124. https://doi.org/10.5059/yukigoseikyokaishi.67.1115
    52. Masato Nozawa, Yuhki Suka, Takashi Hoshi, Toshio Suzuki, Hisahiro Hagiwara. ChemInform Abstract: Total Synthesis of the Hallucinogenic Neoclerodane Diterpenoid Salvinorin A.. ChemInform 2008, 39 (35) https://doi.org/10.1002/chin.200835167
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    Cite this: Org. Lett. 2008, 10, 7, 1365–1368
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol800101v
    Published March 1, 2008
    Copyright © 2008 American Chemical Society
    Request reuse permissions

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