title: Expedient synthesis of α,α-dimethyl-β-hydroxy carbonyl scaffolds via Evans' aldol reaction with a tertiary enolate.
abstract: 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 β-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.
authors: Scripps Institution of Oceanography, University of California San Diego, 9500 Gilman Drive, MC 0212, La Jolla, CA 92093-0212, USA.
authors: Joshawna K
authors: JK
authors: Nunnery
authors: Takashi L
authors: TL
authors: Suyama
authors: Roger G
authors: RG
authors: Linington
authors: William H
authors: WH
authors: Gerwick
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