The total synthesis of swinholide A. Part 3: A stereocontrolled synthesis of (−)-pre-swinholide A.
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Add time:09/01/2019 Source:sciencedirect.com
Two coupling strategies for (−)-pre-swinholide A were devised based on the analysis in Scheme 1. In the first route, a boron-mediated aldol reaction between the ethyl ketone 19 and the aldehyde 3 was used to construct the C15-C16 bond with moderate diastereoselectivity. In the second route, a Mukaiyama aldol reaction between the methyl ketone 54 and the aldehyde 4 introduced the C18-C19 bond with complete stereocontrol.
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