State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China.
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.
Org Lett. 2022 Nov 11;24(44):8104-8108. doi: 10.1021/acs.orglett.2c02834. Epub 2022 Oct 26.
Rugosiformisin A, a skeleton-rearranged abietane-type diterpenoid with a spiro[4.5]decane motif, was isolated from . Its structure was unambiguously established via NMR spectroscopic analysis and single-crystal X-ray diffraction. A bioinspired asymmetric synthesis of rugosiformisin A was achieved in 15 steps with 2.7% overall yield. The synthesis features an iridium-catalyzed asymmetric polyene cyclization and a semipinacol rearrangement.
Rugosiformisin A，一种具有螺[4.5]癸烷骨架的裂环阿替烷型二萜，从 Rugosa sp. 中分离得到。其结构通过 NMR 谱分析和单晶 X 射线衍射得到明确。通过 15 步反应，以 2.7%的总收率，实现了 Rugosiformisin A 的生物启发不对称全合成。该合成方法的特点是铱催化的不对称多烯环化和半频哪醇重排。
