32937-33-0Relevant academic research and scientific papers
Enantioselective Total Syntheses of Manginoids A and C and Guignardones A and C
Zong, Yan,Xu, Ze-Jun,Zhu, Rong-Xiu,Su, Ai-Hong,Liu, Xu-Yuan,Zhu, Ming-Zhu,Han, Jing-Jing,Zhang, Jiao-Zhen,Xu, Yu-Liang,Lou, Hong-Xiang
, p. 15286 - 15290 (2021)
An enantioselective synthetic approach for preparing manginoids and guignardones, two types of biogenetically related meroterpenoids, is reported. This bioinspired and divergent synthesis employs an oxidative 1,3-dicarbonyl radical-initiated cyclization and cyclodehydration of the common precursor to forge the central ring of the manginoids and guignardones, respectively, at a late stage. Key synthetic steps include silica-gel-promoted semipinacol rearrangement to form the 6-oxabicyclo[3.2.1]octane skeleton and the Suzuki–Miyaura reaction of vinyl bromide to achieve fragment coupling. This synthesis protocol enables the asymmetric syntheses of four fungal meroterpenoids from commercially available materials.
