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Updated: May 23, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Divergent Enantioselective Total Synthesis of Aspidosperma Indole Alkaloids
Dong-Xing Tan1,2, Fu-She Han1,2
1College of Chemistry and Material Science, Shandong Agricultural University, No. 61, Daizong Street, Taian, Shandong 271018, China.
Abstract:
We present a collective asymmetric synthesis of 11 aspidosperma indole alkaloids, (-)-aspidospermidine (1), (-)-N-methylaspidospermidine (2), (+)-O-demethylaspidospermine (3), (+)-aspidospermine (4), (-)-eburenine (5), (+)-quebrachamine (6), (-)-vincadifformine (7), (-)-limaspermidine (8), (+)-12-demethoxy-N-acetylcylindrocarine (9), (-)-N-acetylaspidoalbidine (10), and (-)-haplocidine (11), and a formal synthesis of (-)-deoxoapodine (12). The key to our synthesis relied on a desymmetric enantioselective Michael/aldol reaction developed previously by us for the construction of a [3.3.1]-bicyclic ring system of 23 from 1,3-cyclohexadione and a ring-opening/reorganization strategy for the installation of a [6.5.6.5.6] pentacyclic framework 25 bearing different functional groups at N1, C3, C5, and C19, which served as versatile handles for flexible and orthogonal modification at the late stage. Finally, from this common pentacyclic core, divergent syntheses of various aspidosperma alkaloids were accomplished through appropriately orchestrated functional group manipulation. The results presented herein significantly extend the application of our methodology and strategy for the flexible synthesis of aspidosperma alkaloids.
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