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Tetrahydrofurane und γ‐Lactone, VII. Synthese und Reaktionen von γ,γ‐disubstituierten γ‐Lactonen – ein Weg zu funktionalisierten Dodecandisäure‐Derivaten
Author(s) -
Tochtermann Werner,
Weidner Fritjof
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419940609
Subject(s) - chemistry , lactone , cyclopropane , ozonolysis , pyrazoline , medicinal chemistry , methyl iodide , bicyclic molecule , ring (chemistry) , stereochemistry , organic chemistry
Tetrahydrofurans and γ‐Lactones, VII. – Synthesis and Reactions of γ,γ‐Disubstituted γ‐Lactones – an Approach to 4,5‐Functionalized Dodecanedioic Acid Derivatives The title compounds 5 are obtained by Diels‐Alder reaction of cyclooctyne and 2‐substituted furans, subsequent hydrogenation, ozonolysis and oxidation with air. The lactone ring of 6c is opened by treatment with sodium iodide and zinc to give the methylene carbonyl derivative 9a . Compound 9a is converted into the cyclopropane 13 via the pyrazoline 12 .