351187-65-0Relevant academic research and scientific papers
Synthesis of tetrahydrocannabinols based on an indirect 1,4-addition strategy
William, Anthony D.,Kobayashi, Yuichi
, p. 8771 - 8782 (2007/10/03)
The synthetic procedure presented for the preparation of the title compounds requires 1,4-addition of bulky cuprates to cyclohexenones and subsequent reaction with electrophiles. However, the enolates generated by BF3·OEt2-assistance suffer from lack of nucleophilicity. To circumvent this problem, we developed an indirect method consisting of the following three steps: (1) iodination of the cyclohexenones at the α position; (2) BF3·OEt2-assisted 1,4-addition of cuprates (Ar2Cu(CN)-Li2, Ar = aryl) followed by quenching the enolates with water; (3) reaction of the α-iodo-β-arylcylohexanones thus formed with EtMgBr to generate magnesium enolates. The enolates thus generated in this way showed a high reactivity toward ClP(O)(OEt)2 to furnish enol phosphates. The aforementioned procedure was also applied to a synthesis of optically active Δ9-tetrahydrocannabinol. In addition, a naphthalene analogue of the latter compound was also synthesized in a similar way.
A Method to Accomplish a 1,4-Addition Reaction of Bulky Nucleophiles to Enones and Subsequent Formation of Reactive Enolates
William, Anthony D.,Kobayashi, Yuichi
, p. 2017 - 2020 (2007/10/03)
(matrix presented) BF3-promoted 1,4-addition of bulky aryl groups to α-iodo enones, prepared from the parent enones, afforded β-aryl-α-iodo ketones. Subsequent reaction with EtMgBr furnished the magnesium enolates, which upon reactions with CIP
