Pederin: The Metallated Dihydropyran Approach. Stereoselective Reduction ofN-AcylimidatesviaRhodium-Catalysed Hydroboration

Authors:
  • PKPhilip Kocieński
    Philip Kocieński
  • KJKrzysztof Jarowicki
    Krzysztof Jarowicki
  • SMStanislaw Marczak
    Stanislaw Marczak
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Abstract
A synthesis of the insect toxin pederin (1) based upon the union of metallated dihydropyran 8 with the oxamate ester derivative 9 is described. Noteworthy features include (a) a new method for the construction of metallated dihydropyrans which tolerates heteroatom functionality and (b) a rhodium-catalyzed hydroboration reaction which enables stereocontrolled formation of the stereogenic centre at C10.