Direct Entry to 4,10-Didesmethyl (9S)-Dihydroerythronolide A via Catalytic Allene Osmylation

Libing Yu, Huan Wang, Novruz G. Akhmedov, Christopher Sowa, Kai Liu, Hiyun Kim, Lawrence Williams

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

Desmethyl erythronolides have emerged as macrolide targets that may prove effective against resistant bacteria. A five-step sequence to 4,10-didesmethyl (9S)-dihydroerythronolide A (1) from known cyclic bis[allene] 13 is reported. Key structural and mechanistic aspects of the synthesis are discussed along with catalytic allene osmylation. An improved route to 13 is also described.

Original languageEnglish (US)
Pages (from-to)2868-2871
Number of pages4
JournalOrganic letters
Volume18
Issue number12
DOIs
StatePublished - Jun 17 2016

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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