A Concise Synthesis of Mupirocin H Using a Cross-Metathesis-Based Strategy
- Authors
- Sengupta, Sandip; Sim, Taebo
- Issue Date
- 2014-08
- Publisher
- WILEY-V C H VERLAG GMBH
- Citation
- EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v.2014, no.23, pp.5063 - 5070
- Abstract
- A highly efficient (10.1% overall yield) and convergent (longest linear sequence of 16 steps) synthesis of mupirocin H has been achieved, starting from commercially available (+)-(R)-Roche ester. The route relies on an efficient Grubbs cross-metathesis reaction to generate a key, late-stage E-olefin intermediate, and a cobalt-catalysed diastereoselective Reformatsky reaction to produce a beta-hydroxy ester that serves as a late-stage intermediate.
- Keywords
- ENANTIOSELECTIVE SYNTHESIS; REFORMATSKY REACTIONS; DIMETHYL-SULFOXIDE; CHIRAL SYNTHESIS; GENE-CLUSTER; OXIDATION; ALCOHOLS; COBALT; ORGANOBORANES; SELECTIVITY; ENANTIOSELECTIVE SYNTHESIS; REFORMATSKY REACTIONS; DIMETHYL-SULFOXIDE; CHIRAL SYNTHESIS; GENE-CLUSTER; OXIDATION; ALCOHOLS; COBALT; ORGANOBORANES; SELECTIVITY; Total synthesis; Natural products; Polyketides; Metathesis; Reformatsky reaction
- ISSN
- 1434-193X
- URI
- https://pubs.kist.re.kr/handle/201004/126506
- DOI
- 10.1002/ejoc.201402442
- Appears in Collections:
- KIST Article > 2014
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