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Neighbouring‐Group Assisted Thiazole‐Ring Cleavage by DIBAL‐H: An Expeditious Synthesis of Melithiazol C from Myxothiazol A
Author(s) -
Söker Udo,
Sasse Florenz,
Kunze Brigitte,
Höfle Gerhard
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200006)2000:11<2021::aid-ejoc2021>3.0.co;2-k
Subject(s) - chemistry , thiazole , cleavage (geology) , ring (chemistry) , stereochemistry , amide , yield (engineering) , organic chemistry , materials science , geotechnical engineering , fracture (geology) , engineering , metallurgy
The semi‐synthesis of melithiazol C ( 2b ) has been accomplished in 4 steps and 41% overall yield starting from myxothiazol A ( 1a ) produced by fermentation of Myxococcus fulvus . Key steps are a novel reductive cleavage of a thiazole ring by DIBAL‐H and the conversion of the amide 2a into the methyl ester 2b via an imino ester. The biological activities of 2b and of derivatives of its 10‐acetyl group are described.