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Cannabinoid rearrangements: Synthesis of Δ5-tetrahydrocannabinol

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

Publisher: Elsevier Science
Year: 1973
Tongue: French
Weight: 427 KB
Volume: 29
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)83406-2

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✦ Synopsis

1/3,6gEpoxy-hexahydrocannabinol acetate (1) in the presence of borontrifluoride rearranged to 6-oxo-hexahydrocannabinol acetate (3b) and to the aldehyde (4). Hydroboratlon of AE-THC gave the 6-hydroxy hexahydrocannabinols 5a and &I. The latter was converted into A+THC (11). This THC isomer shows no cannabis-type activity in rhesus monkeys.

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