A Biogenetic-Type Synthesis of Cannabifuran and Dehydrocannabifuran

Jorapur, Vaman S.; Duffley, R. P.; Razdan, Raj K.

doi:10.1080/00397918408060722

Cited by 8 publications

(8 citation statements)

References 8 publications

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“…With the completion of the CBM series, we turned our attention toward CBF-based natural products, as shown in Scheme . Although there are several syntheses of CBF ( 3 ) and DCBF ( 4 ) reported, − we were inspired by the unified, biomimetic approach of Razdan, and we hypothesized that this approach might also be extended to CBO ( 6 ). Thus, CBD ( 1 ) was acylated and chemoselectively oxidized to deliver epoxide 15 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of the Cannabimovone and Cannabifuran Class of Minor Phytocannabinoids and Their Anti-inflammatory Activity

et al. 2022

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Despite centuries-long use of Cannabis in human culture and the now ubiquitous claims of its medicinal value, only a small handful of phytocannabinoids have been rigorously evaluated for pharmacological properties. While more than 100 distinct minor cannabinoids have been documented to date, a paucity of studies on their biological activities have been conducted due to a lack of routine access to sufficient quantities for testing. Herein, we report a strategy to prepare several structurally diverse minor cannabinoids deriving synthetically from readily available cannabidiol. Furthermore, we examined their ability to polarize activated microglia toward an antiinflammatory phenotype using LPS-stimulated BV2 microglial cells. The minor cannabinoids studied, especially cannabielsoin, dehydrocannabielsoin, cannabimovone, and 3′-epicannabimovone, inhibited the production of prototypical pro-inflammatory biomarkers. This study represents the beginning of a systematic mapping of the roles minor cannabinoids may play in the medicinal properties of cannabis used for the treatment of pain and inflammation.

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Section: Resultsmentioning

confidence: 99%

Synthesis of the Cannabimovone and Cannabifuran Class of Minor Phytocannabinoids and Their Anti-inflammatory Activity

et al. 2022

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“…Compounds 9-13 were identified as cannabispirone [ 12 ], β-cannabispiranol [ 15 ], dehydrocannabifuran [ 16 ], [ 17 ], cannflavin B [ 9 ] and cannabigerol [ 9 ] by comparing their spectroscopic data with reported values. However, this is the first report for the 13 C-NMR assignments for dehydrocannabifuran (11) (Table 3).…”

Section: Resultsmentioning

confidence: 99%

Isolation and Characterization of New Cannabis Constituents from a High Potency Variety

Radwan¹,

Rosenberg²,

Slade³

et al. 2008

Planta Med

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Phytochemical investigation of a high potency variety of Cannabis sativa L. resulted in the isolation of six new metabolites, (±)-6,7-trans-epoxycannabigerolic acid (2), (±)-6,7-cisepoxycannabigerolic acid (3), (±)-6,7-cis-epoxycannabigerol (4), (±)-6,7-trans-epoxycannabigerol (5), 5′-methyl-4-pentylbiphenyl-2,2′,6-triol (7), and 7-methoxycannabispirone (8), along with seven known compounds namely, cannabigerolic acid (1), 5′-methoxycannabigerolic acid (6), cannabispirone (9), β-cannabispiranol (10), dehydrocannabifuran (11), cannflavin B (12) and cannabigerol (13). The antimicrobial as well as the antileishmanial activities were investigated.

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“…In view of these results we decided to test our method in the synthesis of natural dibenzofurans and we selected as our target the minor cannabis constituent cannabifuran 1h 15 (Scheme 3). The latter compound was previously prepared by a variety of methods including acid catalyzed intramolecular cyclization of biphenyls, 4c,d transformation of the natural cannabidiol in the dibenzofuran 14 framework and cycloaddition or benzannulation of benzofuran derivatives. 6c,f,g In this work we propose a different synthetic approach in which both the furan ring and one aromatic ring are formed in a single annulation step.…”

Section: R= O-methoxyaryl R= Hydrogen Alkyl Vinyl Aryl Heteroarylmentioning

confidence: 99%

A New Preparative Route to Substituted Dibenzofurans by Benzannulation Reaction. An Application to the Synthesis of Cannabifuran

Serra¹,

Fuganti²

2003

Synlett

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A N e w R o u t e t o S u b s t i t u t e d D i b e n z o f u r a n s Abstract: A new regioselective pathway to substituted dibenzofuran derivatives is described here. According to this procedure substituted 1-acetoxy-3-alkoxycarbonyl dibenzofurans are obtained by treatment of 6-(2-methoxyaryl)-3-alkoxycarbonylhex-3-en-5-ynoic acids with acetic anhydride in the presence of sodium acetate. The latter acids are prepared from the easily available substituted o-iodo-anisoles by Sonogashira coupling with propargylic alcohol and Wittig reaction as the key steps. The described benzannulation reaction proceeds in regioselective fashion and a range of substituents are tolerated. Its synthetic utility is demonstrated by a new synthesis of cannabifuran, a naturally occurring dibenzofuran.

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A Biogenetic-Type Synthesis of Cannabifuran and Dehydrocannabifuran

Cited by 8 publications

References 8 publications

Synthesis of the Cannabimovone and Cannabifuran Class of Minor Phytocannabinoids and Their Anti-inflammatory Activity

Synthesis of the Cannabimovone and Cannabifuran Class of Minor Phytocannabinoids and Their Anti-inflammatory Activity

Isolation and Characterization of New Cannabis Constituents from a High Potency Variety

A New Preparative Route to Substituted Dibenzofurans by Benzannulation Reaction. An Application to the Synthesis of Cannabifuran

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