화학공학소재연구정보센터
Journal of the American Chemical Society, Vol.131, No.22, 7560-7560, 2009
Nazarov Cyclization Initiated by Peracid Oxidation: The Total Synthesis of (+/-)-Rocaglamide
The total syntheses of aglafolin, rocagloic acid, and rocaglamide using Nazarov cyclization are described. Generation of the necessary oxyallyl cation intermediate was accomplished via peracid oxidation of an allenol ether to generate an unusual oxycarbenium ion species that undergoes cyclization. The synthesis is efficient, highly diastereoselective, and strategically distinct from previous syntheses of rocaglamide.