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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.
- Source :
-
Journal of the American Chemical Society [J Am Chem Soc] 2017 Oct 04; Vol. 139 (39), pp. 13882-13896. Date of Electronic Publication: 2017 Sep 20. - Publication Year :
- 2017
-
Abstract
- The secondary metabolites that comprise the diterpenoid alkaloids are categorized into C <subscript>18</subscript> , C <subscript>19</subscript> , and C <subscript>20</subscript> 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 C <subscript>18</subscript> (weisaconitine D), one C <subscript>19</subscript> (liljestrandinine), and three C <subscript>20</subscript> (cochlearenine, paniculamine, and N-ethyl-1α-hydroxy-17-veratroyldictyzine) natural products from a common intermediate.
Details
- Language :
- English
- ISSN :
- 1520-5126
- Volume :
- 139
- Issue :
- 39
- Database :
- MEDLINE
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 28858498
- Full Text :
- https://doi.org/10.1021/jacs.7b07706