Title:
脱メチル化工程を含むフィトカンナビノイドの合成
Document Type and Number:
Japanese Patent JP2020530855
Kind Code:
A
Abstract:
式Ｉのメチル化フィトカンナビノイド化合物を脱メチル化して式ＩＩのフィトカンナビノイド化合物を形成するための方法であって、メチル化フィトカンナビノイド化合物の少なくとも一部を脱メチル化し、フィトカンナビノイド化合物を形成するのに十分な時間、溶解無機アルカリ塩の存在下でメチル化フィトカンナビノイド化合物および極性非プロトン性溶媒を含む反応混合物を加熱する工程を含む、方法。【化１】（式中、Ｒ１は、置換または非置換Ｃ１〜Ｃ５アルキルからなる群から選択され、Ｒ２は、ＯＨまたはＯからなる群から選択され、Ｒ３は、置換もしくは非置換シクロヘキセン、置換もしくは非置換Ｃ２〜Ｃ８アルケンまたは置換もしくは非置換Ｃ２〜Ｃ８ジアルケンからなる群から選択されるか、またはＲ２はＯであり、Ｒ２およびＲ３は一緒になって、Ｒ２が内環原子である環構造を形成している）
Inventors:
Leaky, Tristan
Scott, Michael
Cassiu, Michael
Scott, Michael
Cassiu, Michael
Application Number:
JP2020509082A
Publication Date:
October 29, 2020
Filing Date:
August 16, 2018
Export Citation:
Assignee:
UNIVERSITY OF SYDNEY
International Classes:
C07C51/09; C07C65/05; C07D311/58; C07D311/80; C07D311/94
Other References:
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DARBY, CRYSTAL M. ET AL: "Whole cell screen for inhibitors of pH homeostasis in Mycobacterium tuberculosis", PLOS ONE, vol. 8 (7), JPN6021011786, 2013, pages 68942, ISSN: 0004477583
MANDI, ATTILA ET AL: "Reducing Molecular Flexibility by Cyclization for Elucidation of Absolute Configuration by CD Calcul", CHIRALITY, vol. 28 (6), JPN6021011789, 2016, pages 453 - 459, ISSN: 0004477584
DETHE, DATTATRAYA H. ET AL: "Enantiospecific Syntheses of Hongoquercins A and B and Chromazonarol", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2017 (7), JPN6021011792, 2017, pages 1143 - 1150, ISSN: 0004477585
KURDYUMOV, ALEKSEY V.; HSUNG, RICHARD P.; IHLEN, KIRSTEN; WANG, JIASHI: "Formal [3 + 3] Cycloaddition Approach to Chromenes and Chromanes. Concise (±)-Daurichromenic Ester", ORGANIC LETTERS, vol. 5 (21), JPN6021011795, 2003, pages 3935 - 3938, ISSN: 0004477586
HU, HONGJUAN; HARRISON, TYLER J.; WILSON, PETER D.: "A Modular and Concise Total Synthesis of (±)-Daurichromenic Acid and Analogues", JOURNAL OF ORGANIC CHEMISTRY, vol. 69 (11), JPN6021011798, 2004, pages 3782 - 3786, ISSN: 0004477587
CROMBIE, LESLIE; CROMBIE, W. MARY L.: "Cannabinoid acids and esters: miniaturized synthesis and chromatographic study", PHYTOCHEMISTRY, vol. 16 (9), JPN6021011801, 1977, pages 1413 - 1420, ISSN: 0004477588
DARBY, CRYSTAL M. ET AL: "Whole cell screen for inhibitors of pH homeostasis in Mycobacterium tuberculosis", PLOS ONE, vol. 8 (7), JPN6021011786, 2013, pages 68942, ISSN: 0004477583
MANDI, ATTILA ET AL: "Reducing Molecular Flexibility by Cyclization for Elucidation of Absolute Configuration by CD Calcul", CHIRALITY, vol. 28 (6), JPN6021011789, 2016, pages 453 - 459, ISSN: 0004477584
DETHE, DATTATRAYA H. ET AL: "Enantiospecific Syntheses of Hongoquercins A and B and Chromazonarol", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2017 (7), JPN6021011792, 2017, pages 1143 - 1150, ISSN: 0004477585
KURDYUMOV, ALEKSEY V.; HSUNG, RICHARD P.; IHLEN, KIRSTEN; WANG, JIASHI: "Formal [3 + 3] Cycloaddition Approach to Chromenes and Chromanes. Concise (±)-Daurichromenic Ester", ORGANIC LETTERS, vol. 5 (21), JPN6021011795, 2003, pages 3935 - 3938, ISSN: 0004477586
HU, HONGJUAN; HARRISON, TYLER J.; WILSON, PETER D.: "A Modular and Concise Total Synthesis of (±)-Daurichromenic Acid and Analogues", JOURNAL OF ORGANIC CHEMISTRY, vol. 69 (11), JPN6021011798, 2004, pages 3782 - 3786, ISSN: 0004477587
CROMBIE, LESLIE; CROMBIE, W. MARY L.: "Cannabinoid acids and esters: miniaturized synthesis and chromatographic study", PHYTOCHEMISTRY, vol. 16 (9), JPN6021011801, 1977, pages 1413 - 1420, ISSN: 0004477588
Attorney, Agent or Firm:
Yoshiyuki Inaba
Toshifumi Onuki
Akihiko Eguchi
Kazuhiko Naito
Toshifumi Onuki
Akihiko Eguchi
Kazuhiko Naito