Direct entry to erythronolides via a cyclic bis[allene]

Kai Liu, Hiyun Kim, Partha Ghosh, Novruz G. Akhmedov, Lawrence J. Williams

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

The complexity and low tractability of antibiotic macrolides pose serious challenges to addressing the problem of resistance through semi- or total synthesis. Here we describe a new strategy involving the preparation of a complex yet tractable macrocycle and the transformation of this macrocycle into a range of erythronolide congeners. These compounds represent valuable sectors of erythromycinoid structure space and constitute intermediates with the potential to provide further purchase in this space. The routes are short. The erythronolides were prepared in three or fewer steps from the macrocycle, which was prepared in a longest linear sequence of 11 steps.

Original languageEnglish (US)
Pages (from-to)14968-14971
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number38
DOIs
StatePublished - Sep 28 2011

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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