Total synthesis of (±)-batzelladine K: A biomimetic approach

Nafees Ahmed, Keyur G. Brahmbhatt, Inder Pal Singh, Kamlesh K. Bhutani

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Abstract

Total synthesis of batzelladine K was achieved by a biomimetic approach. The key reactions involve two Wittig reactions of phosphoranes and aldehydes leading to an ,-unsaturated ketone, followed by a condensation with guanidine. The synthesis was accomplished in four steps with an overall yield of 12%. The relative stereochemistry of batzelladine K was established by NOE experiments and comparison with literature values.

Original languageEnglish
Article numberZ07910SS
Pages (from-to)2567-2570
Number of pages4
JournalSynthesis
Issue number15
DOIs
Publication statusPublished - 2010
Externally publishedYes

Keywords

  • batzelladines
  • biomimetic synthesis
  • marine natural products
  • phosphorane
  • tricyclic guanidine

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