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Synthesis of Novel Tetraacetal Oxa‐Cage Compounds from 2‐Methylthiofurans
Author(s) -
Lin ChuChung,
Huang FangJung,
Lin JuneChieh,
Wu HsienJen
Publication year - 1996
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199600026
Subject(s) - chemistry , ozonolysis , cage , adduct , sequence (biology) , stereochemistry , medicinal chemistry , sulfide , carbon atom , oxygen atom , organic chemistry , molecule , ring (chemistry) , biochemistry , mathematics , combinatorics
Several novel tetraacetal oxa‐cage compounds 9a‐9f were synthesized from the corresponding 2‐methylthiofurans la‐lf by a short sequence. The structures of these tetraoxa‐cage compounds were deduced from their spectral data and proven by X‐ray analysis of 9a . Ozonolysis of the endo adducts 5a‐5f in CH 2 C1 2 at −78 °C followed by reduction with dimethyl sulfide gave the tetraoxa‐cages 9a‐9f in 65‐75% yields, respectively. Ozonolysis of the exo adduct 6a under the same reaction conditions gave the tetracarbonyl compound 10 . The phenylthio group substituted tetraoxa‐cage 13 and the tetraacetal oxa‐cage 17, with one more carbon atom on the apex position, were also synthesized in a similar sequence.