Syntheses of Polycyclic Tetrahydrofurans by Cascade Reactions Consisting of Five-Membered Ring Selective Prins Cyclization and Friedel–Crafts Cyclization

Autor:	Yuji Suzuki, Kazuhiko Takatori, Megumi Mizukami, Shinji Nagumo, Yuki Sakata, Eiko Yasui
Rok vydání:	2018
Předmět:	Indole test 010405 organic chemistry Organic Chemistry Aromaticity Prins reaction 010402 general chemistry Ring (chemistry) 01 natural sciences Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Cascade reaction Furan Divergent synthesis Friedel–Crafts reaction
Zdroj:	The Journal of Organic Chemistry. 83:9103-9118
ISSN:	1520-6904 0022-3263
Popis:	A novel cascade reaction consisting of a five-membered ring selective Prins cyclization and a subsequent Friedel–Crafts cyclization is reported. Treatment of homocinnamyl alcohols and aromatic aldehydes with BF3·OEt2 in CH2Cl2 afforded hydrocyclopentafurans. Also hydrocyclopentafurans underwent the same cascade reaction after its furan ring cleavage upon treatment with BF3·OEt2 at room temperature. Various combinations of hydropentafurans and aromatic aldehydes or indole aldehydes permitted divergent synthesis of diquinane-furans stuck in aromatic rings.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::c807af723ee01aef54e1b1e0ac0f1c7b https://doi.org/10.1021/acs.joc.8b01195 Zobrazit plný text záznamu