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A highly advanced enantiomerically pure C(1)-C(18) precursor of the larger fragment of the macrodiolide pamamycin-607 has been synthesized. The stereotriad C(7)-C(9) between the two heterocyclic rings of the target was generated using a diastereoselective hydroboration controlled by minimization of allylic 1,3-strain.
Using sultone chemistry, a short and highly enantioselective synthesis of an advanced precursor for the larger hydroxy acid moiety and of the complete smaller hydroxy acid portion of the macrodiolide antibiotic pamamycin-607 has been accomplished.
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