Synthesis of the Originally Proposed Structure of Palmerolide C

Gordon John Florence, Joanna Wlochal

Research output: Contribution to journalLetterpeer-review

20 Citations (Scopus)

Abstract

A stereoselective synthesis of the proposed structure of palmerolide C (2), a cytotoxic marine macrolide isolated from the Antarctic tunicate Synoicum adareanum, utilizes a convergent carbonyl-based coupling strategy to construct the C1-C24 carbon skeleton. Compound 2 was shown to be a diastereomer of palmerolide C, and the structural revision of the natural product is proposed.
Original languageEnglish
Pages (from-to)14250-14254
Number of pages5
JournalChemistry - A European Journal
Volume18
Issue number45
DOIs
Publication statusPublished - 5 Nov 2012

Keywords

  • REVISED STRUCTURES
  • VINYLOGOUS ALDOL
  • structure elucidation
  • natural products
  • melanoma
  • CHEMICAL-SYNTHESIS
  • FRAGMENT
  • total synthesis
  • COUPLING-CONSTANTS
  • macrolide
  • TUNICATE SYNOICUM-ADAREANUM
  • ACYCLIC STRUCTURES
  • NATURAL-PRODUCTS
  • FORMAL TOTAL-SYNTHESIS
  • BIOLOGICAL EVALUATION

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