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Kondensierte Dithiole, III. Synthese von 1,2‐Dithiolo‐furanen
Author(s) -
Stachel HansDietrich,
Zoukas Thomas,
Hußlein Manfred,
Nienaber Julyane,
Schorp Matthias
Publication year - 1993
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.199319930151
Subject(s) - chemistry , ketone , ring (chemistry) , stereochemistry , lactone , contraction (grammar) , medicinal chemistry , organic chemistry , medicine
Ring‐Fused 1,2‐Dithioles, III. – Synthesis of 1,2‐Dithiolo‐furans A series of 1,3‐dithiino‐furans 4/9 has been synthesized by starting with the β‐ketoester 5a or the cyclic ketone 5b . The dithiines undergo oxidative ring contraction to give the corresponding 1,2‐dithiolo‐furans 3/14 . The ester function of 3h is easily removed to give 2 , the oxaanalog of the antibiotic thiolutine. In general, the lactone group is the most sensitive part in compounds 3 , 4 and 14 . In marked contrast the dithiine 9a is cleaved by amines at the thioketale site forming the tetronic acid derivatives 10a/b .