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Highly stereoselective synthesis of mupirocin H
- Source :
- Tetrahedron. 73:1182-1189
- Publication Year :
- 2017
- Publisher :
- Elsevier BV, 2017.
-
Abstract
- A highly diastereoselective and efficient convergent synthesis of mupirocin H starting from (+)-(R)-Roche ester was achieved. Grubbs cross metathesis was employed as the key step in the pathway to generate an important E-olefin intermediate. Other processes utilized in the route include a Pd-catalysed stereoselective substitution reaction of a cis epoxide, Sharpless epoxidation followed by Red-Al promoted epoxide ring opening, and Seebach methylation and a TEMPO/BAIB mediated oxidation-lactonization sequence. Finally, we observed that mupirocin H inhibits SbnE, a synthetase required for staphyloferrin B biosynthesis.
- Subjects :
- Substitution reaction
Sharpless epoxidation
010405 organic chemistry
Chemistry
Stereochemistry
Organic Chemistry
Convergent synthesis
Epoxide
Mupirocin
010402 general chemistry
Metathesis
01 natural sciences
Biochemistry
0104 chemical sciences
chemistry.chemical_compound
Biosynthesis
Drug Discovery
Stereoselectivity
Subjects
Details
- ISSN :
- 00404020
- Volume :
- 73
- Database :
- OpenAIRE
- Journal :
- Tetrahedron
- Accession number :
- edsair.doi...........30faf25973a597fbb8f523e49c33e717