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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.

Authors :
Kou KGM
Kulyk S
Marth CJ
Lee JC
Doering NA
Li BX
Gallego GM
Lebold TP
Sarpong R
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