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Tetrahydrofurane und γ‐Lactone, III. γ‐Lactone mit funktionalisierten γ‐ständigen Seitenketten aus Cyclooctin nnd Furan
Author(s) -
Scholz Gerhard,
Konusch Joachim,
Tochtermann Werner
Publication year - 1990
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.1990199001109
Subject(s) - chemistry , pyridinium chlorochromate , furan , lactone , ozonolysis , aldehyde , side chain , borane , pyridinium , stereochemistry , organic chemistry , polymer , catalysis
Tetrahydrofurans and γ‐Lactones, III. — γ‐Lactones with Functionalized γ‐Side Chains from Cyclooctyne and Furan The oxanorbornadiene 1 , easily available from cyclooctyne and furan, is converted in three simple steps (hydrogenation, ozonolysis, and oxidation by air) to the γ‐substituted γ‐lactone 4a with a carbonyl and a carboxyl group in the side chain. The corresponding methyl ester 4b gives by diastereoselective reduction the esters (±)‐ syn ‐ and anti ‐ 5 , which are fully characterized as pure crystalline compounds. Reduction of 4a with borane and subsequent oxidation with pyridinium chlorochromate leads to the aldehyde 4d via hydroxylated derivatives.