Alexander Pulis - Short Stereoselective Synthesis of the Phytophthora Universal Mating Hormone Alpha 1 using Lithiation/Borylation Reactions

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      Publication Details (including relevant citation   information):

      Angew.   Chem. Int. Ed. 2014,   53, 4382-4385

      DOI:   10.1002/anie.201400714

        A. P.   Pulis, P.   Fackler and V. K. Aggarwal

      Abstract:

      The universal mating hormone α1 of the virulent   plant pathogen Phytophthora has been synthesized in 12   steps and 28% overall yield. Key   C-C 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.

      Address (URL): http://onlinelibrary.wiley.com/doi/10.1002/anie.201400714/abstract