Synthesis of the C(1)-C(12) segment of peloruside A by an alpha-benzyloxymethyl ketone aldol strategy |
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| Authors: | Engers Darren W Bassindale Martin J Pagenkopf Brian L |
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| Institution: | Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX 78712, USA. |
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| Abstract: | The C(1)-C(12) segment of 16-membered antitumor macrolide peloruside A has been prepared by a BF(3).OEt(2)-catalyzed Mukaiyama aldol reaction between a glucose-derived C(1)-C(7) aldehyde and a C(8)-C(12) alpha-benzyloxymethyl ketone. Exclusive 2,3-anti and moderate 3,5-anti/syn facial selectivity (3.5:1) was observed in the aldol reaction. The key C(1)-C(7) aldehyde contains the required stereochemistry at carbons two, three, and five, and has been efficiently prepared on multigram scales from commercial triacetyl D-glucal. reaction: see text] |
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