Enrichment of a Diastereomer in Magnolan
    2.
    发明公开

    公开(公告)号:US20230286937A1

    公开(公告)日:2023-09-14

    申请号:US18019782

    申请日:2021-08-12

    申请人: Symrise AG

    IPC分类号: C07D319/08 C11B9/00

    CPC分类号: C07D319/08 C11B9/008

    摘要: The invention relates to a distillative process for the preparation of a diastereomer-enriched odorant mixture, and to the diastereomer-enriched odorant mixture and its use as an odorant or for the preparation of an odorant composition. Furthermore, the invention relates to the use of the diastereomer-enriched odorant mixture for imparting, modifying or enhancing a floral odour note of a perfumed product or for the preparation of a perfumed product. Finally, the present invention also relates to odorant compositions and perfumed products comprising the diastereomer-enriched odorant composition.

    Process for the production of cannabinoids

    公开(公告)号:US11407724B2

    公开(公告)日:2022-08-09

    申请号:US17269722

    申请日:2019-08-20

    摘要: A process for the preparation of substantially pure diverse known and novel cannabinoids 1 and 2, which include Δ9-tetrahydrocannabinol (7), tetrahydrocannabivarin (9), cannabidiol (11), cannabidivarin (12) and other naturally occurring tetracyclic and tricyclic cannabinoids and other synthetic tetracyclic and tricyclic analogues, via intermediates 3, 6, 4 and 5, using a cascade sequence of allylic rearrangement, aromatization and, for the tetracyclic cannabinoids, further highly stereoselective and regioselective cyclization. These synthesized cannabinoids can more easily be obtained at high purity levels than cannabinoids isolated or synthesized via known methods. The cannabinoids 2, including Δ9-tetrahydrocannabinol (7), tetrahydrocannabivarin (9), are obtained containing very low levels of isomeric cannabinoids such as the undesirable Δ8-tetrahydrocannabinol. The known and novel analogues with variation in aromatic ring substituents, whilst easily synthesized with the new methodology, would be much more difficult to make from any of the components of cannabis or cannabis oil.

    Novel Cannabinoids and Cannabinoid Acids and Their Derivatives

    公开(公告)号:US20210238157A1

    公开(公告)日:2021-08-05

    申请号:US17269732

    申请日:2019-08-20

    摘要: The present invention relates to novel cannabinoids 1 and 2, synthesized from simple starting materials using a cascade sequence of allylic rearrangement, aromatization and, for tetracyclic cannabinoids, further highly stereoselective and regioselective cyclization. These synthesized cannabinoids can more easily be obtained at high purity levels than cannabinoids isolated or synthesized via known methods. The cannabinoids 2 are obtained containing very low levels of isomeric cannabinoids such as the undesirable Δ8-tetrahydrocannabinol. The analogues with variation in aromatic ring substituents, whilst easily synthesized with the new methodology, would be much more difficult to make from any of the components of cannabis oil. Novel compounds of the formulas 3, 4, 5 and 6, as intermediates for the synthesis of the cannabinoids of the formulas 1 and 2 are also disclosed.

    Facile and Selective Perfluoro- And Polyfluoroarylation of Meldrum's Acid

    公开(公告)号:US20190256488A1

    公开(公告)日:2019-08-22

    申请号:US16404110

    申请日:2019-05-06

    摘要: This disclosure relates generally to the facile and selective mono-perfluoro and poly-fluoroarylation of Meldrum's acid to generate a versatile synthon for highly fluorinated alpha-phenyl acetic acid derivatives which provide straightforward access to fluorinated building blocks. The reaction takes place quickly and all products were isolated without the need for chromatography. An embodiment provides an alternative strategy to access alpha-arylated Meldrum's acids which avoids the need for aryl-Pb(IV) salts or diaryliodonium salts and provides access to the tertiary product which was not previously synthetically accessible. The synthetic versatility and utility of the Meldrum's acid products is demonstrated by subjecting the products to several derivatizations of the Meldrum's acid products as well as photocatalytic hydrodefluorination which provide access to difficult but valuable synthetic targets such as multifluorinated aromatics.