Literature DB >> 30033728

Lewis-Acid-Mediated Union of Epoxy-Carvone Diastereomers with Anisole Derivatives: Mechanistic Insight and Application to the Synthesis of Non-natural CBD Analogues.

Sophia J Bailey, Rishi R Sapkota, Alexandra E Golliher, Barry Dungan, Marat Talipov, F Omar Holguin, William A Maio.   

Abstract

The use of trimethylsilyl trifluoromethanesulfonate as a mild means to unite epoxy-carvone silyl ethers with anisole derivatives to yield products that are structurally similar to the CBD scaffold is reported. Importantly, unlike related methods, this process can utilize both epoxy-carvone diastereomers and does not require the use of air/moisture-sensitive organometallic reagents. Several examples of aryl nucleophiles as well as mechanistic insight based on in silico computational analysis are presented.

Entities:  

Year:  2018        PMID： 30033728     DOI： 10.1021/acs.orglett.8b01909

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  2 in total

1.  Using (+)-Carvone to access novel derivatives of (+)-ent-Cannabidiol: the first asymmetric syntheses of (+)-ent-CBDP and (+)-ent-CBDV.

Authors:  Alexandra E Golliher; Antonio J Tenorio; Nina O Dimauro; Nicolas R Mairata; F Omar Holguin; William Maio
Journal:  Tetrahedron Lett       Date:  2021-02-05       Impact factor: 2.415

2.  A Revised Modular Approach to (-)-trans-Δ8-THC and Derivatives Through Late-Stage Suzuki-Miyaura Cross-Coupling Reactions.

Authors:  Victor R L J Bloemendal; Daan Sondag; Hidde Elferink; Thomas J Boltje; Jan C M van Hest; Floris P J T Rutjes
Journal:  European J Org Chem       Date:  2019-03-18
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.