A Strategy toward the Biomimetic Synthesis of (+/-)-Morusalbanol A Pentamethyl Ether

作者:Tee Jia Ti; Keane Theo; Meijer Anthony J H M; Khaledi Hamid; Abd Rahman Noorsaadah; Chee Chin Fei
来源:Synthesis (Germany), 2016, 48(14): 2263-2270.
DOI:10.1055/s-0035-1560434

摘要

A strategy toward the biomimetic synthesis of morusalbanol A pentamethyl ether is described. The synthesis is based on a hydrogen-bond-assisted Diels-Alder cycloaddition between a dehydroprenyl diene and a chalcone dienophile. Selective cleavage of the ortho-methyl ether of the resulting cycloadduct allows rotation of the C3-C21 bond and subsequent intramolecular cyclization affords the pentamethyl ether of (+/-)-morusalbanol A. As with the natural product, morusalbanol A, a number of key proton and carbon signals are absent in the NMR spectra of the title product.

  • 出版日期2016-7