Synthesis of (-)-okilactomycin by a prins-type fragment-assembly strategy

Jason M. Tenenbaum, William J. Morris, Daniel W. Custar, Karl A. Scheidt

Research output: Contribution to journalArticlepeer-review

30 Scopus citations

Abstract

All things converge: A highly convergent synthesis of (-)-okilactomycin utilizes a Prins-type Maitland-Japp cyclization for the fragment assembly of two complex intermediates (see scheme). The synthesis also employs a highly diastereoselective Lewis acid promoted Diels-Alder reaction and an olefin ring-closing metathesis to close a strained 11-membered macrocycle.

Original languageEnglish (US)
Pages (from-to)5892-5895
Number of pages4
JournalAngewandte Chemie - International Edition
Volume50
Issue number26
DOIs
StatePublished - Jun 20 2011

Keywords

  • Maitland-Japp reaction
  • Prins reaction
  • natural products
  • tetrahydropyrans
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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