674769-31-4Relevant articles and documents
Synthesis of the C(1)-C(12) segment of peloruside A by an α-benzyloxymethyl ketone aldol strategy
Engers, Darren W.,Bassindale, Martin J.,Pagenkopf, Brian L.
, p. 663 - 666 (2007/10/03)
The C(1)-C(12) segment of 16-membered antitumor macrolide peloruside A has been prepared by a BF3·OEt2-catalyzed Mukaiyama aldol reaction between a glucose-derived C(1)-C(7) aldehyde and a C(8)-C(12) α-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.