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Org Lett. 2017 Sep 15;19(18):4980-4983. doi: 10.1021/acs.orglett.7b02476. Epub 2017 Aug 31.

Scalable Synthesis of a Key Intermediate for the Production of Pleuromutilin-Based Antibiotics.

Author information

1
Department of Chemistry, Yale University , New Haven, Connecticut 06520, United States.
2
Department of Pharmacology, Yale School of Medicine , New Haven, Connecticut 06520, United States.

Abstract

An improved synthesis of an eneimide, which is a useful precursor to pleuromutilin-based antibiotics, is reported. This synthesis proceeds in six steps and 17% overall yield (27% based on recovery of a key hydrindenone intermediate) and requires two fewer chromatography steps and five fewer days of reaction time than the previously reported route. The use of expensive, acutely toxic, and precious metal reagents or catalysts has been minimized.

PMID:
28858512
DOI:
10.1021/acs.orglett.7b02476
[Indexed for MEDLINE]

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