Synthesis of the C(1)-C(12) segment of peloruside A by an alpha-benzyloxymethyl ketone aldol strategy.
Org Lett, 2004/3/04;6(5):663-6.
Engers DW[1], Bassindale MJ, Pagenkopf BL
Affiliations
PMID: 14986944
Impact factor: 6.072
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]
MeSH terms
Aldehydes; Animals; Antineoplastic Agents; Bridged Bicyclo Compounds, Heterocyclic; Catalysis; Ketones; Lactones; Macrolides; Molecular Structure; Porifera; Stereoisomerism
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