A Unifying Synthesis Approach to the C(18)-, C(19)-, and C(20)-Diterpenoid Alkaloids.

A Unifying Synthesis Approach to the C(18)-, C(19)-, and C(20)-Diterpenoid Alkaloids.
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DOI:
10.1021/jacs.7b07706
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发表时间:
2017-10-04
影响因子:
15
通讯作者:
Sarpong R
Sarpong R
中科院分区:
化学1区
文献类型:
--
作者:
Kou KGM;Kulyk S;Marth CJ;Lee JC;Doering NA;Li BX;Gallego GM;Lebold TP;Sarpong R

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包含二萜生物碱的次生代谢物根据构成其中心框架的连续碳原子的数量分为 C18、C19 和 C20 家族。在此,我们详细介绍了通过化学合成(包括光化学方法)制备这些分子的努力,以及最终的生物启发策略,该策略导致从常见中间体统一合成一种 C18(魏沙乌碱 D)、一种 C19(liljestrandinine)和三种 C20(cochlearenine、paniculamine 和 N-乙基-1α-羟基-17-veratroyldictyzine)天然产物。
The secondary metabolites that comprise the diterpenoid alkaloids are categorized into C18, C19, and C20 families depending on the number of contiguous carbon atoms that constitute their central framework. Herein, we detail our efforts to prepare these molecules by chemical synthesis, including a photochemical approach, and ultimately a bioinspired strategy that has resulted in the development of a unifying synthesis of one C18 (weisaconitine D), one C19 (liljestrandinine), and three C20 (cochlearenine, paniculamine, and N-ethyl-1α-hydroxy-17-veratroyldictyzine) natural products from a common intermediate.
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