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Synthese mittlerer und großer Ringe, XXXV [1] . Funktionalisierte Hydroazulenone durch transannulare Cyclisierungen von 10‐Oxo‐3,6‐hexanooxepin‐4,5‐dicarbonsäure‐dimethylester
Author(s) -
Tochtermann Werner,
Habeck Thorsten,
Wolff Christian,
Peters EvaMaria,
Peters Karl,
Schnering Hans Georg Von
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931261219
Subject(s) - chemistry , sodium methoxide , stereochemistry , intramolecular force , yield (engineering) , medicinal chemistry , methanol , organic chemistry , materials science , metallurgy
Synthesis of Medium and Large Rings, XXXV [1] . – Functionalized Hydroazulenones by Transannular Cyclizations of Dimethyl 10‐Oxo‐3,6‐hexanooxepine‐4,5‐dicarboxylate Two differently bridged hydroazulenones 2 and 3 are obtained in 69 and 61% yield, respectively, by treatment of the title compound 1 with sodium methoxide. The course of these intramolecular transannular cyclizations strongly depends on the amount of added base. 2 is hydrogenated to the ketones 9 and 10 . Oxidative cleavage of the enol ether double bond of 3 and 10 leads to the octahydroazulene‐1,6‐dione 11 and to the decahydroazulene‐3,8‐dione 12 , respectively.