Total Syntheses of Dysidealactams E and F and Dysidealactone B, Drimane-Type Sesquiterpenes Derived from a Dysidea sp. of Marine Sponge.

Autor: Chen, Yuhao, Lan, Ping, White, Lorenzo V., Yang, Weiguang, Banwell, Martin G.
Předmět:
Zdroj: Synlett; Jul2023, Vol. 34 Issue 12, p1529-1533, 5p
Abstrakt: Keywords: cycloaddition; drimanes; marine natural products; sesquiterpenes; total synthesis EN cycloaddition drimanes marine natural products sesquiterpenes total synthesis 1529 1533 5 07/11/23 20230725 NES 230725 Graph Drimane-type sesquiterpenes are encountered in numerous plants, fungi, and marine organisms, including mollusks and sponges. Reports on the synthesis of drimane-type sesquiterpenes abound, permitting us to draw upon a large body of literature [1][16] in establishing a reliable route to the target compounds B 4 b , B 5 b , and B 7 b . Heating this compound in refluxing trifluoroacetic acid (TFA) resulted in efficient formation of the cyclic acid anhydride (±)- B 8 b , the structure of which was confirmed by single-crystal X-ray analysis [34] [see also the Supporting Information (SI)]. [47] The establishment of methods for the enantioselective synthesis of the Diels-Alder adduct B 12 b and thereby providing access to both the (+)- and (-)-forms of anhydride B 8 b , would serve to enhance the capacity to explore drimane-type chemical space. [Extracted from the article]
Databáze: Complementary Index