Cannabinoid rearrangements. Synthesis of Δ5-tetrahydrocannabinol

R. Mechoulam; Z. Ben-Zvi; H. Varconi; Y. Samuelov

doi:10.1016/S0040-4020(01)83406-2

Cannabinoid rearrangements. Synthesis of Δ⁵-tetrahydrocannabinol

R. Mechoulam, Z. Ben-Zvi, H. Varconi, Y. Samuelov

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

17 Scopus citations

Abstract

1β,6β-Epoxy-hexahydrocannabinol acetate (1) in the presence of borontrifluoride rearranged to 6-oxo-hexahydrocannabinol acetate (3b) and to the aldehyde (4). Hydroboration of Δ⁶-THC gave the 6-hydroxy hexahydrocannabinols 5a and 8a. The latter was converted into Δ⁵-THC (11). This THC isomer shows no cannabis-type activity in rhesus monkeys.

Original language	English
Pages (from-to)	1615-1619
Number of pages	5
Journal	Tetrahedron
Volume	29
Issue number	11
DOIs	https://doi.org/10.1016/S0040-4020(01)83406-2
State	Published - 1973
Externally published	Yes

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title = "Cannabinoid rearrangements. Synthesis of Δ5-tetrahydrocannabinol",

abstract = "1β,6β-Epoxy-hexahydrocannabinol acetate (1) in the presence of borontrifluoride rearranged to 6-oxo-hexahydrocannabinol acetate (3b) and to the aldehyde (4). Hydroboration of Δ6-THC gave the 6-hydroxy hexahydrocannabinols 5a and 8a. The latter was converted into Δ5-THC (11). This THC isomer shows no cannabis-type activity in rhesus monkeys.",

author = "R. Mechoulam and Z. Ben-Zvi and H. Varconi and Y. Samuelov",

note = "Funding Information: Acknowledgements-This work was supported by the U.S. National Instituteo f Mental Health and Smith Kline and French Laboratories,P hiladelphia,t o whom we express our thanks.W e ase also gratefult o Prof. H. Edery and Dr. Y Grunfeld for the monkeyt ests.",

year = "1973",

doi = "10.1016/S0040-4020(01)83406-2",

language = "English",

volume = "29",

pages = "1615--1619",

journal = "Tetrahedron",

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T1 - Cannabinoid rearrangements. Synthesis of Δ5-tetrahydrocannabinol

AU - Mechoulam, R.

AU - Ben-Zvi, Z.

AU - Varconi, H.

AU - Samuelov, Y.

N1 - Funding Information: Acknowledgements-This work was supported by the U.S. National Instituteo f Mental Health and Smith Kline and French Laboratories,P hiladelphia,t o whom we express our thanks.W e ase also gratefult o Prof. H. Edery and Dr. Y Grunfeld for the monkeyt ests.

PY - 1973

Y1 - 1973

N2 - 1β,6β-Epoxy-hexahydrocannabinol acetate (1) in the presence of borontrifluoride rearranged to 6-oxo-hexahydrocannabinol acetate (3b) and to the aldehyde (4). Hydroboration of Δ6-THC gave the 6-hydroxy hexahydrocannabinols 5a and 8a. The latter was converted into Δ5-THC (11). This THC isomer shows no cannabis-type activity in rhesus monkeys.

AB - 1β,6β-Epoxy-hexahydrocannabinol acetate (1) in the presence of borontrifluoride rearranged to 6-oxo-hexahydrocannabinol acetate (3b) and to the aldehyde (4). Hydroboration of Δ6-THC gave the 6-hydroxy hexahydrocannabinols 5a and 8a. The latter was converted into Δ5-THC (11). This THC isomer shows no cannabis-type activity in rhesus monkeys.

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DO - 10.1016/S0040-4020(01)83406-2

M3 - Article

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SN - 0040-4020

VL - 29

SP - 1615

EP - 1619

JO - Tetrahedron

JF - Tetrahedron

IS - 11

ER -

Cannabinoid rearrangements. Synthesis of Δ5-tetrahydrocannabinol

Abstract

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Cannabinoid rearrangements. Synthesis of Δ⁵-tetrahydrocannabinol