BiBr3-Mediated Intramolecular Aza-Prins Cyclization of Aza-Achmatowicz Rearrangement Products: Asymmetric Total Synthesis of Suaveoline and Sarpagine Alkaloids,Angewandte Chemie International Edition

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BiBr3-Mediated Intramolecular Aza-Prins Cyclization of Aza-Achmatowicz Rearrangement Products: Asymmetric Total Synthesis of Suaveoline and Sarpagine Alkaloids
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2023-09-19 , DOI: 10.1002/anie.202311671
Wai Fung Cheng ₁ , Shiqiang Ma ₁ , Yin Tung Lai ₁ , Yuen Tsz Cheung ₁ , Kornkamon Akkarasereenon ₁ , Yiqin Zhou ₁ , Rongbiao Tong ₁

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An intramolecular Prins cyclization of aza-Achmatowicz rearrangement products was developed to construct the versatile 9-azabicyclo[3.3.1]nonane (9-ABN) ring system with a variety of substitution patterns and then applied to the asymmetric total synthesis of six suaveoline and sarpagine alkaloids: macrophylline, suaveoline, norsuaveoline, affinisine, normacusine B and N_a-Me-16-epipericyclivine.

中文翻译：

BiBr3 介导的 Aza-Achmatowicz 重排产物的分子内 Aza-Prins 环化：Suaveoline 和 Sarpagine 生物碱的不对称全合成

开发了 aza-Achmatowicz 重排产物的分子内 Prins 环化，以构建具有多种取代模式的通用 9-氮杂双环[3.3.1]壬烷 (9-ABN) 环系统，然后应用于六种 Suaveoline 和沙帕津生物碱：大茶碱、甜甜碱、去苏甜碱、阿菲尼辛、正马库辛 B 和N _a -Me-16-表哌环利文。

更新日期：2023-09-19

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