Short Stereoselective Synthesis of the Phytophthora Universal Mating Hormone alpha 1 Using Lithiation/Borylation Reactions

Alexander P. Pulis, Philipp Fackler, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

16 Citations (Scopus)
323 Downloads (Pure)

Abstract

The universal mating hormone 1 of the virulent plant pathogen Phytophthora has been synthesized in 12 steps and 28% overall yield. Key CC bond-forming steps involved the use of two lithiation/borylation reactions to couple together enantioenriched building blocks, one of which also set up the stereochemistry of the tertiary alcohol at C11. Detailed analysis showed that the diastereomeric purity of the target molecule was >91%, the highest obtained to date.

Original languageEnglish
Pages (from-to)4382-4385
Number of pages4
JournalAngewandte Chemie - International Edition
Volume53
Issue number17
DOIs
Publication statusPublished - 22 Apr 2014

Keywords

  • asymmetric synthesis
  • boron
  • lithium
  • natural products
  • total synthesis
  • 4 STEREOISOMERS
  • BORONIC ESTERS
  • ALPHA-1
  • BORANES

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