Isolation and Bioinspired Synthesis of Lauenones A and B, Skeleton-Rearranged Diterpenoids with Antiadipogenic Activity from Croton laui

作者：Zongyi Zhang, Yuhan Chen, Cheng‐Yu Zheng, Yuan Gao, Yao‐Yue Fan, Jian‐Min Yue, Jin‐Xin Zhao · 发表于：Organic Letters · 年份：2025 · DOI：10.1021/acs.orglett.5c00445 · 被引用次数：9 · 研究领域：Bioactive Natural Diterpenoids Research、Plant biochemistry and biosynthesis、Traditional and Medicinal Uses of Annonaceae

Two skeleton-rearranged labdane diterpenoids, lauenones A ( 1 ) and B ( 2 ) were isolated from Croton laui . Their bioinspired synthesis was accomplished in 9 and 10 steps, respectively, without using any protecting groups. Key steps include a semipinacol rearrangement and a substrate-controlled one-pot reaction cascade involving photooxidation and aldol condensation. Notably, both lauenones A and B exhibit antiadipogenesis in 3T3-L1 adipocytes by downregulating the differentiation factors and liposynthesis enzymes at mRNA transcription and protein expression levels.