U. Soker et al., Neighbouring-group assisted thiazole-ring cleavage by DIBAL-H: An expeditious synthesis of melithiazol C from myxothiazol A, EUR J ORG C, (11), 2000, pp. 2021-2026
The semi-synthesis of melithiazol C (2b) has been accomplished in 4 steps a
nd 41% overall yield starting from myxothiazol A (la) produced by fermentat
ion of Myxococcus fulvus. Key steps are a novel reductive cleavage of a thi
azole ring by DIBAL-H and the conversion of the amide 2a into the methyl es
ter 2b via an imino ester. The biological activities of 2b and of derivativ
es of its 10-acetyl group are described.