Applications of [4+2] Anionic Annulation and Carbonyl-Ene Reaction in the Synthesis of Anthraquinones, Tetrahydroanthraquinones, and Pyranonaphthoquinones

Autor:	Shyam Basak, Dipakranjan Mal
Rok vydání:	2017
Předmět:	Annulation 010405 organic chemistry Organic Chemistry 010402 general chemistry 01 natural sciences Dehydroherbarin 0104 chemical sciences chemistry.chemical_compound chemistry Intramolecular force Anthraquinones Organic chemistry Isomerization Ene reaction
Zdroj:	The Journal of Organic Chemistry. 82:11035-11051
ISSN:	1520-6904 0022-3263
Popis:	Hexa-2,5-dienoates, susceptible to isomerization by acids and bases, are suitable for the [4+2] anionic annulation to give 3-(2-alkenyl)naphthoates in regiospecific manner. When combined with intramolecular carbonyl-ene reaction (ICE), the accessibility of the naphthoates culminates in a new synthesis of anthraquinones and diastereoselective synthesis of tetrahydroanthraquinones. This strategy has also resulted in a 3-step synthesis of dehydroherbarin from a 3-methallylnaphthoate.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::1addbe63eb82e83338cbb7b7694e618e https://doi.org/10.1021/acs.joc.7b01987 Zobrazit plný text záznamu