Neighbouring-group assisted thiazole-ring cleavage by DIBAL-H: An expeditious synthesis of melithiazol C from myxothiazol A

Authors
Soker, U Sasse, F Kunze, B Hofle, G
Citation
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
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
11
Year of publication
2000
Pages
2021 - 2026
Database
ISI
SICI code
1434-193X(200006):11<2021:NATCBD>2.0.ZU;2-Z
Abstract
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.