926014-25-7Relevant academic research and scientific papers
Total synthesis of (±)-merrilactone A via catalytic Nazarov cyclization
He, Wei,Huang, Jie,Sun, Xiufeng,Frontier, Alison J.
, p. 498 - 499 (2007)
The total synthesis of merrilactone A (a neurotrophic agent) has been achieved. In the approach reported, simultaneous creation of the C-4 and C-5 stereocenters was accomplished stereospecifically using an unprecedented variant of the Nazarov cyclization. Additional studies focused upon this Lewis acid-catalyzed cyclization of a silyloxyfuran-containing intermediate are presented. Copyright
Total synthesis of (±)-merrilactone A
He, Wei,Huang, Jie,Sun, Xiufeng,Frontier, Alison J.
, p. 300 - 308 (2008/09/18)
The total synthesis of racemic merrilactone A (a neurotrophic agent) is described, featuring simultaneous and stereospecific creation of the C4 and C5 Stereocenters via a notable silyloxyfuran Nazarov cyclization. Full details of the successful synthetic strategy are given, as well as several examples of the interesting reactivity of intermediates that were prepared and studied during the execution of the total synthesis. A detailed investigation of the Lewis acid-catalyzed Nazarov cyclization of silyloxyfurans was conducted, including a systematic study of substrate scope and limitations. In addition, experiments were conducted that suggest the participation of Lewis acidic silicon species in the Nazarov cyclization.
