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Search for "Veratrum alkaloids" in Full Text gives 1 result(s) in Beilstein Journal of Organic Chemistry.

Recent advancements in the synthesis of Veratrum alkaloids

Morwenna Mögel,
David Berger and
Philipp Heretsch

Beilstein J. Org. Chem. 2025, 21, 2657–2693, doi:10.3762/bjoc.21.206

Morwenna Mogel David Berger Philipp Heretsch Institut für Organische Chemie, Leibniz Universität Hannover, Schneiderberg 1b, 30167 Hannover, Germany 10.3762/bjoc.21.206 Abstract The Veratrum alkaloids constitute a class of natural products with particularly intricate polycyclic frameworks and

functionalization for rapid access to these exceptional alkaloids, while also showcasing the evolution of the art of synthesis and its ability in meeting the demands posed by molecular complexity. Keywords: alkaloid synthesis; convergent synthesis; total synthesis; Veratrum alkaloids; Introduction Veratrum

representatives (Scheme 1), the steroidal C27-cholestane backbone is easily recognizable, except for a rearranged 14(13→12)abeo-cholestane in the Veratrum alkaloids. This C-nor-D-homo-framework represents a unique distinction from the other classes, requiring different and creative approaches for its synthesis

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Graphical Abstract

Scheme 1: Representatives of steroid alkaloid classes. Marked in blue is the steroidal cholestane framework, ...

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Scheme 2: Subclasses of Veratrum alkaloids: jervanine, veratramine and cevanine-type [8].

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Scheme 3: Flow chart presentation of the synthesis of (−)-englerin A developed by the Christmann group [10].

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Scheme 4: Structures and year of synthesis of the three types of Veratrum alkaloids reported in the literatur...

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Scheme 5: Key step in the synthesis of cyclopamine (6) by the Giannis group [21].

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Scheme 6: Overview of the semisynthesis of cyclopamine (6) reported by the Giannis group in 2009 [21].

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Scheme 7: Key steps in the synthesis of cyclopamine (6) by the Baran group [23].

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Scheme 8: Overview of the total synthesis of cyclopamine (6) by the Baran group in 2023 [23].

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Scheme 9: Key steps in the synthesis of cyclopamine (6) by the Zhu/Gao group [25].

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Scheme 10: Overview of the total synthesis of cyclopamine (6) by the group of Zhao/Gao in 2023 [25].

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Scheme 11: Key steps in the synthesis of cyclopamine (6) by the Liu/Qin group [26].

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Scheme 12: Overview of the semisynthesis of cyclopamine (6) by the Liu/Qin group in 2024 [26].

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Scheme 13: Key steps in the synthesis of jervine (12) by the Masamune group [14].

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Scheme 14: Overview of the total synthesis of jervine (12) by the Masamune group in 1968 [14].

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Scheme 15: Color-coded schemes of the presented cyclopamine (6) syntheses by Giannis, Baran, Zhu/Gao, and Liu/...

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Scheme 16: Key steps in the total synthesis of veratramine (13) by the Johnson group [15].

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Scheme 17: Overview of the total synthesis of veratramine (13) by the Johnson group in 1967 [15].

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Scheme 18: Key steps in the synthesis of veratramine (13) by the Zhu/Gao group [25].

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Scheme 19: Shortened overview of the total synthesis of veratramine (13) by the Zhu/Gao group in 2023 [25].

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Scheme 20: Key steps in the synthesis of veratramine by the Liu/Qin group [26].

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Scheme 21: Overview of the semisynthesis of veratramine (13) by the Liu/Qin group in 2024 [26].

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Scheme 22: Key steps in the synthesis of veratramine (13) by the Trauner group [27].

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Scheme 23: Overview of the total synthesis of veratramine (13) by the Trauner group in 2025 [27].

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Scheme 24: Key steps in the synthesis of verarine (14) by the Kutney group [16-19].

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Scheme 25: Overview of the total synthesis of verarine (14) by the Kutney group reported 1962–1968 [16-19].

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Scheme 26: Color-coded schemes of the presented veratramine-type alkaloid synthesis of Zhu/Gao, Liu/Qin and Tr...

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Scheme 27: Structures of veracevine (86), veratridine (87), and cevadine (88).

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Scheme 28: Key step in the semisynthesis of verticine (15) by the Kutney group (1977) [20,46].

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Scheme 29: Overview of the semisynthesis of verticine (15) by the Kutney group (1977) [20,46].

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Scheme 30: Key step of the total synthesis of (±)-4-methylenegermine (17) by the Stork group (2017) [22].

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Scheme 31: Overview of the total synthesis of (±)-4-methylenegermine (17) by the Stork group (2017) [22].

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Scheme 32: Key step of the total synthesis of heilonine (16) by Cassaidy and Rawal (2021) [24].

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Scheme 33: Overview of the total synthesis of heilonine (16) by Cassaidy and Rawal (2021) [24]. FGI: functional gr...

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Scheme 34: Key steps of the synthesis of heilonine (16) by Dai and co-workers (2024) [28].

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Scheme 35: Overview of the total synthesis of heilonine (16) by Dai and co-workers (2024) [28].

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Scheme 36: Key steps of the total synthesis of zygadenine (18) reported by Luo and co-workers [29].

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Scheme 37: Overview of the total synthesis of zygadenine (18) by Luo and co-workers (2023) [29].

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Scheme 38: Key step of the divergent total syntheses of highly oxidized cevanine-type alkaloids by Luo and co-...

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Scheme 39: Divergent syntheses of highly oxidized cevanine-type alkaloids by Luo and co-workers (2024) [30].

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Scheme 40: Color-coded overview of the presented cevanine-type alkaloid syntheses [10,20,22,24,28-30,46]. LLS: longest linear sequen...

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Published 10 Dec 2025

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