A Concise Synthesis of Mupirocin H Using a Cross-Metathesis-Based Strategy

Authors
Sengupta, SandipSim, 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
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KIST Article > 2014
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