Yehiel Gaoni

Hashish—IV: The isolation and structure of cannabinolic cannabidiolic and cannabigerolic acids☆

Abstract The methyl esters of cannabinolic, cannabidiolic and cannabigerolic acids are shown to possess structures, VIb, IVb and Ib respectively.

Hashish—VII : The isomerization of cannabidiol to tetrahydrocannabinols

Abstract Depending on the reaction conditions used, the physiologically active products obtained by Adams on isomerization of the inactive cannabidiol (Ia) with acids are shown to be either Δ 1(6) tetrahydrocannabinol (II) or a mixture of II, Δ 1 tetrahydrocannabinol (IIIa) and the two isomers of 1-ethoxy hexahydrocannabinol (VIIIa, VIIIb).

cis-2,4-methanoglutamate is a potent and selective N-methyl-D-aspartate receptor agonist

Cis- and trans-2,4-methanoglutamate were compared with L-glutamate as acidic amino acid ligands. Cis-2,4-methanoglutamate had a Ki of 0.052 microM against N-methyl-D-aspartate (NMDA)-specific L-[3H]glutamate binding compared with 0.050 microM for L-glutamate. Cis-2,4-methanoglutamate exhibited no significant affinity against [3H]kainate or [3H]alpha-amino-3-hydroxy-5-methyl-4-isoxazole propionate ([3H]AMPA) binding. Trans-2,4-methanoglutamate had no significant affinity for any of these sites. Cis-2,4-methanoglutamate increased [3H]N-1[2-thienyl]cyclohexyl-3,4-piperidine [( 3H]TCP) binding with EC50 of 0.35 +/- 0.14 microM. It produced an inward current in rat brain mRNA-injected Xenopus oocytes which was blocked by the NMDA antagonist, D-2-amino-7-phosphonoheptanoate (D-AP7). Cis-2,4-methanoglutamate (EC50 = 15.9 microM) was 100-fold more potent than L-glutamate (EC50 = 1,584 microM) in reducing the excitatory postsynaptic potential in CA1 of hippocampal slices. Cis-2,4-methanoglutamate is the most potent, selective NMDA agonist known.

Lithium aluminium hydride promoted extrusion of SO2 from sulfolenes and sulfolene-adducts. 1,3-dienes, 3-chloro- and 3,3-dichloro-1,4-dienes and skipped polyenes

Bei der Behandlung mit Lithiumalanat werden Sulfolene sowie Sulfolen- Addukte unter Eliminierung von Schwefeldioxid in entsprechende Diene ubergefuhrt.

Base induced isomerizations of λ,δ-epoxyketones—II: Syntheses in the thujane series. d,l-sabina ketone and d,l-cis-sabinene hydrate☆

Abstract Base treatment of 4-(epoxyisopropylidene)cyclohexanone provides an entry into the bicyclo-[3.1.0]alkane series. In this way d,l-sabina ketone, d,l-cis-sabinene hydrate and a few related bicyclic compounds were synthesized.

Hashish—XIII : On the nature of the beam test☆

Abstract The purple colour produced by treatment of cannabidiol (I) with 5% ethanolic potassium hydroxide (Beam test) is due to the anions of the hydroxy-quinone II and its dimer III. Compounds II and III are formed from I by air oxidation during the reaction. The quinone III is reduced in the mass spectrometer to a M + + 4 species (probably the dihydroquinone).

SYNTHESIS OF AMINOCYCLOBUTANE MONO- AND DICARBOXYLIC ACIDS AND DERIVATIVES THEREOF FROM (PHENYLSULFONYL)BICYCLOBUTANES

(1995). SYNTHESIS OF AMINOCYCLOBUTANE MONO- AND DICARBOXYLIC ACIDS AND DERIVATIVES THEREOF FROM (PHENYLSULFONYL)BICYCLOBUTANES. Organic Preparations and Procedures International: Vol. 27, No. 2, pp. 185-212.

Regiospecific additions of hydrazoic acid and benzylamine to 1-(arylsulfonyl)bicyclo[1.1.0]Butanes. Application to the synthesis of cis and trans 2,7-methanoglutamic acids

Addition of hydrazoic acid or benzylamine to 1-(arylsulfonyl) bicyclobutanes introduces the nitrogen nucleophlle at position 3 of the derived cyclobutane, even when a carboxyl derivative is present at this position as a second activating group. Precursors of α-amino cyclobutane carboxylic acids may thus be obtained and these can be further transformed to the title diacids via carbonylation α to the sulfone and reduction.

New bridgehead-substituted 1-(arylsulfonyl)bicyclo[1.1.0]butanes and some novel addition reactions of the bicyclic system

Abstract In view of planned syntheses of target cyclobutane derivatives, a series of new 3-substituted bicyclobutanes was prepared from sulfones 1–7. Some novel addition reactions involving the central bond were then applied to several of the new compounds as well as to some previously described bicyclobutanes. These reactions include the additions of hydrazoic acid, of cyanocuprate reagents other than methyl reagents, and of phenylselenol, as well as single examples of addition of phenylselenyl azide and of lithium bromide. Several 3-allylated bicyclobutane derivatives were transformed into 1-(arylsulfonyl)bicyclo[2.1.1]hexanes by conversion to cyclobutanes, epoxidation and intramolecular base-induced cyclization.

Base induced isomerization of λ,δ-epoxyketones—III: Synthesis and reactions of some norcarane derivatives☆

Abstract Base treatment of epoxykarahanaenone ( 1 ) yields 5- endo -hydroxy-3,3,6-trimethylnorcarane-2-one ( 2 ). Dehydration of 2 with potassium hydrogen sulfate leads, partly, to [3.2.0]bicyclic ketones. Reaction of 2 with tosyl chloride in pyridine substitutes the 5-hydroxyl with chlorine; thionyl chloride in pyridine yields mainly bis-ethers of 2 . Other reactions of 2 are described.