Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5217116 | Tetrahedron | 2013 | 10 Pages |
Abstract
Stereoselective synthesis of an advanced intermediate towards the highly cytotoxic polyketide metabolite spirangien A was achieved. A key step in the synthesis was installation of the C23 stereocentre by a substrate controlled C22-23 aldol reaction. Comparison of this result with previous literature reports suggests that the facial preference of the aldehyde controls the outcome of the C22-23 aldol coupling and depends on the O27/25 protecting groups when reacting with complex ketones, which contain the C17-15 stereochemistry.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Claire Gregg, Michael V. Perkins,