Cannabinoid rearrangements. Synthesis of Δ5-tetrahydrocannabinol

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

Research output: Contribution to journalArticlepeer-review

16 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 languageEnglish
Pages (from-to)1615-1619
Number of pages5
JournalTetrahedron
Volume29
Issue number11
DOIs
StatePublished - 1 Jan 1973
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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