Isolation and Bioinspired Total Synthesis of Rugosiformisin A, A Skeleton-Rearranged Abietane-Type Diterpenoid from Isodon rugosiformis
Isolation and Bioinspired Total Synthesis of Rugosiformisin A, A Skeleton-Rearranged Abietane-Type Diterpenoid from Isodon rugosiformis
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Rugosiformisin A（一种来自 Isodon rugosiformis 的骨架重排的松香烷型二萜）的分离和仿生全合成
DOI：
10.1021/acs.orglett.2c02834
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发表时间：
2022
期刊：
影响因子：
5.2
通讯作者：
Pema-Tenzin Puno
中科院分区：
文献类型：
--
作者：
Bin Wang;Hua-Yi Jiang;Jin Yang;Jun Li;Bing-Chao Yan;Xi Chen;Kun Hu;Xing-Ren Li;Han-Dong Sun;Jun Deng;Pema-Tenzin Puno
Rugosiformisin A是一种具有螺旋[4.5]十烷基序的骨架重排的二萜型二萜，从misodon rugosiformis中分离得到。通过核磁共振波谱分析和单晶x射线衍射确定了其结构。通过15步合成了rugosiformisin A，总收率为2.7%。该合成具有铱催化的不对称多烯环化和半品萘重排的特点。
Rugosiformisin A, a skeleton-rearranged abietane-type diterpenoid with a spiro[4.5]decane motif, was isolated fromIsodon rugosiformis. 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.