Synthesis of Octahydroperylene, the Framework of Altertoxin III.

Autor: Gutsche, Maximilian, Podlech, Joachim
Předmět:
Zdroj: European Journal of Organic Chemistry; 1/15/2024, Vol. 27 Issue 3, p1-6, 6p
Abstrakt: Routes to the framework of perylenequinone‐derived mycotoxins of the dihydroanthracene type are described. Starting with anthracene derivatives, attachment of C3 units at positions 9 and 10 and twofold cyclization would furnish the required pentacycle. Heck‐type couplings, SN2 additions of enolates, alkynyl and allyl additions turned out to be not successful, while addition of a Grignard reagent prepared from acetal‐protected 3‐bromopropionaldehyde to anthraflavic acid methyl ester, subsequent acetal cleavage, and Birch reduction furnished octahydroperylene in only four steps. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index