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Expedient synthesis of @a,@a-dimethyl-@b-hydroxy carbonyl scaffolds via Evans' aldol reaction with a tertiary enolate

Joshawna K Nunnery, Takashi L Suyama, Roger G Linington, and William H Gerwick

Tetrahedron Lett 52(23):4 (2011) PMID 21617761 PMCID PMC3100194

An efficient synthetic methodology for 3-hydroxy-2,2-dimethyloctynoic acid (DHOYA) and several variants, which are increasingly common fragments encountered in bioactive marine cyanobacterial metabolites, was developed. These fragments were obtained in three steps via a tertiary aldol reaction utilizing an Evans' chiral auxiliary to afford the desired stereochemistry at the @b-hydroxy carbon. Thus far, this methodology has been successfully applied in determination of the absolute stereochemistry of eight cyanobacterial natural products, including the VGSC activator palymramide A.

Copyright © 2011 Elsevier Ltd. All rights reserved.

DOI: 10.1016/j.tetlet.2011.03.126
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