137059-80-4Relevant academic research and scientific papers
High pressure Diels-Alder approach to hydroxy-substituted 6a-cyano-tetrahydro-6H-benzo[c]chromen-6-ones: A route to Δ6- cis-cannabidiol
Ballerini, Eleonora,Minuti, Lucio,Piermatti, Oriana,Pizzo, Ferdinando
, p. 4311 - 4317 (2009)
(Chemical Equation Presented) Diels-Alder cycloaddition reactions of 3-cyanocoumarin, hydroxy-substituted 3-cyanocoumarins and mesyl-substituted 3-cyano-coumarins with methyl-1,3-butadienes carried out under high pressure (11 kbar) are reported. Activatio
Experimental and computational studies into an ATPH-Promoted exo-selective IMDA reaction: A short total synthesis of Δ9-THC
Pearson, Emma L.,Kanizaj, Nicholas,Willis, Anthony C.,Paddon-Row, Michael N.,Sherburn, Michael S.
supporting information; experimental part, p. 8280 - 8284 (2010/10/02)
(Figure Presented) Reversal of fortune: The inherent cis stereoselectivity of an intramolecular Diels-Alder reaction is reversed through promotion with aluminum tris(2,6-diphenylphenoxide) (ATPH), allowing a total synthesis of the natural product Δ9
High-pressure diels-alder cycloadditions between benzylideneacetones and 1,3-Butadienes: Application to the synthesis of (R,R)-(-)- and (S,S)-(+)-Δ8-tetrahydrocannabinol
Ballerini, Eleonora,Minuti, Lucio,Piermatti, Oriana
supporting information; scheme or table, p. 4251 - 4260 (2010/09/05)
High-pressure Diels-Alder reactions of various alkoxy/alkyl-substituted benzylideneacetones with methyl-1,3-butadienes are reported. Activation by high pressure (8-11 kbar) in combination with the mild Lewis acid HfCl 42THF allows these reactions to efficiently and regioselectively produce a series of ortho-substituted cyclohexenyl-benzene cycloadducts, that are useful precursors for the expeditious construction of the privileged 6,6-dimethyltetrahydro-6H-benzo[c]chromene skeleton. Application to the synthesis of Δ8-trans-THC in both enantiomeric pure forms is based on the successful resolution of selected cycloadduct by the SAMP-hydrazone method.
