1. Enantioselective Total Syntheses of Manginoids A and C and Guignardones A and C
- Author
-
Ai-Hong Su, Jing-Jing Han, Jiao-Zhen Zhang, Xu-Yuan Liu, Hong-Xiang Lou, Ze-Jun Xu, Yuliang Xu, Yan Zong, Rongxiu Zhu, and Ming-Zhu Zhu
- Subjects
010405 organic chemistry ,Chemistry ,Stereochemistry ,Vinyl bromide ,Enantioselective synthesis ,Late stage ,Total synthesis ,General Medicine ,General Chemistry ,010402 general chemistry ,Ring (chemistry) ,01 natural sciences ,Catalysis ,0104 chemical sciences ,Semipinacol rearrangement ,chemistry.chemical_compound ,Divergent synthesis ,Octane - Abstract
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.
- Published
- 2021