Synthese mittlerer und großer Ringe, XXXV [1] . Funktionalisierte Hydroazulenone durch transannulare Cyclisierungen von 10‐Oxo‐3,6‐hexanooxepin‐4,5‐dicarbonsäure‐dimethylester | Zendy

Tochtermann Werner | Zendy; Habeck Thorsten | Zendy; Wolff Christian | Zendy; Peters EvaMaria | Zendy; Peters Karl | Zendy; Schnering Hans Georg Von | Zendy

Premium

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research