Total syntheses of cannabidiol and Δ1-tetrahydrocannabinol metabolites

Naftali Lander; Zvi Ben-Zvi; Raphael Mechoulam; Bill Martin; Marrianne Nordqvist; Stig Agurell

doi:10.1039/p19760000008

Total syntheses of cannabidiol and Δ¹-tetrahydrocannabinol metabolites

Naftali Lander
, Zvi Ben-Zvi
, Raphael Mechoulam
, Bill Martin
, Marrianne Nordqvist
, Stig Agurell

Research output: Contribution to journal › Article › peer-review

28 Scopus citations

Abstract

10-Hydroxycannabidiol [2-(10-hydroxy-p-mentha-1,8-dien-3-yl)-5- pentylresorcinol] (Va), which has tentatively been identified as a cannabidiol metabolite, as well as 6α- and 6β-hydroxy-cannabidiol [(VIa) and (VIIa)], which are now reported to be metabolites, have been prepared from cannabidiol. Total syntheses of 7-hydroxycannabidiol triacetate (IIIb) and 7-acetoxy-Δ¹-tetrahydrocannabinol (9-acetoxymethyl-6a,7,8,10a- tetrahydro-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol) (IIc) from p-mentha-1,8-dien-7-ol are described.

Original language	English
Pages (from-to)	8-16
Number of pages	9
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	1
DOIs	https://doi.org/10.1039/p19760000008
State	Published - 1976
Externally published	Yes

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title = "Total syntheses of cannabidiol and Δ1-tetrahydrocannabinol metabolites",

abstract = "10-Hydroxycannabidiol [2-(10-hydroxy-p-mentha-1,8-dien-3-yl)-5- pentylresorcinol] (Va), which has tentatively been identified as a cannabidiol metabolite, as well as 6α- and 6β-hydroxy-cannabidiol [(VIa) and (VIIa)], which are now reported to be metabolites, have been prepared from cannabidiol. Total syntheses of 7-hydroxycannabidiol triacetate (IIIb) and 7-acetoxy-Δ1-tetrahydrocannabinol (9-acetoxymethyl-6a,7,8,10a- tetrahydro-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol) (IIc) from p-mentha-1,8-dien-7-ol are described.",

author = "Naftali Lander and Zvi Ben-Zvi and Raphael Mechoulam and Bill Martin and Marrianne Nordqvist and Stig Agurell",

year = "1976",

doi = "10.1039/p19760000008",

language = "English",

pages = "8--16",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

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publisher = "Chemical Society",

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T1 - Total syntheses of cannabidiol and Δ1-tetrahydrocannabinol metabolites

AU - Lander, Naftali

AU - Ben-Zvi, Zvi

AU - Mechoulam, Raphael

AU - Martin, Bill

AU - Nordqvist, Marrianne

AU - Agurell, Stig

PY - 1976

Y1 - 1976

N2 - 10-Hydroxycannabidiol [2-(10-hydroxy-p-mentha-1,8-dien-3-yl)-5- pentylresorcinol] (Va), which has tentatively been identified as a cannabidiol metabolite, as well as 6α- and 6β-hydroxy-cannabidiol [(VIa) and (VIIa)], which are now reported to be metabolites, have been prepared from cannabidiol. Total syntheses of 7-hydroxycannabidiol triacetate (IIIb) and 7-acetoxy-Δ1-tetrahydrocannabinol (9-acetoxymethyl-6a,7,8,10a- tetrahydro-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol) (IIc) from p-mentha-1,8-dien-7-ol are described.

AB - 10-Hydroxycannabidiol [2-(10-hydroxy-p-mentha-1,8-dien-3-yl)-5- pentylresorcinol] (Va), which has tentatively been identified as a cannabidiol metabolite, as well as 6α- and 6β-hydroxy-cannabidiol [(VIa) and (VIIa)], which are now reported to be metabolites, have been prepared from cannabidiol. Total syntheses of 7-hydroxycannabidiol triacetate (IIIb) and 7-acetoxy-Δ1-tetrahydrocannabinol (9-acetoxymethyl-6a,7,8,10a- tetrahydro-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol) (IIc) from p-mentha-1,8-dien-7-ol are described.

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DO - 10.1039/p19760000008

M3 - Article

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AN - SCOPUS:0016887564

SN - 1472-7781

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JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 1

ER -

Total syntheses of cannabidiol and Δ1-tetrahydrocannabinol metabolites

Abstract

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Total syntheses of cannabidiol and Δ¹-tetrahydrocannabinol metabolites