135503-45-6Relevant academic research and scientific papers
Efficient Synthesis of (1S,5S)-4-Alkyl-6,6-dimethylbicyclohept-3-en-2-ones from (1R,5S)-(+)-Nopinone and Preparation of Some Chiral Building Blocks Suitable for the Asymmetric Synthesis
Watanabe, Masataka,Awen, Bahlul Z.,Kato, Michiharu
, p. 3923 - 3927 (2007/10/02)
A general and convenient transformation of (1R,5S)-(+)-nopinone (1) into (1S,5S)-4-alkyl-6,6-dimethylbicyclohept-3-en-2-ones, i.e. (-)-verbenone (6a) as the simplest compound and its C(4)-alkyl homologs 6b-f, via (+)-apoverbenone (7) is developed and applied, starting with 6a,e, to the syntheses of (4R,5R)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene (12a) and (4R,5S)- and (4R,5R)-1-acetoxy-5-(3-butenyl)-4-isopropenyl-5-methyl-1-cyclohexene (12b and 12c), in connection with a search for chiral building blocks suitable for the asymmetric synthesis.Preparation of 12a indicates the formal synthesis of the elemanoid sesquiterpenes (-)-β-elemenone and (-)-eleman-8β,12-olide
Synthesis of Racemic and Optically Active Δ9-Tetrahydrocannabinol (THC) Metabolites
Siegel, Craig,Gordon, Patrick M.,Uliss, David B.,Handrick, G. Richard,Dalzell, Haldean C.,Razdan, Raj. K.
, p. 6865 - 6872 (2007/10/02)
The preparation of racemic and optically active Δ9-THC metabolites is described from synthon 13.Racemic synthon 13 is prepared in four steps (46percent) from Danishefsky's diene.Optically active synthon 13 is prepared from perillaldehyde via the enone 22 in six steps (23percent yield).Alternatively, nopinone can be converted to 13 in three steps (50percent yield) via a cyclobutane ring cleavage.The acid-catalyzed condensation of 13 with olivetol (6a) and subsequent conversion to 11-hydroxy and 9-carboxyl Δ9-THC metabolites 2a and 4a is described, as well as the preparation of 1',1'-dimethylheptyl THC analogues 2b, 3b, and 4 b from 5-(1',1'-dimethylheptyl)resorcinol (6c).
