Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 67, Issue 25, Pages 8783-8788Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo020402k
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Funding
- NIGMS NIH HHS [GM 53386] Funding Source: Medline
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Chelation-controlled reduction of chiral beta-alkoxy ketones containing a competing beta'-oxygen functionality has been investigated. Various syn-1,3-diols were prepared conveniently by reduction of beta-alkoxy ketones with LiI/LiAlH4 (syn:anti selectivity up to > 99: 1). The corresponding beta-alkoxy ketones were derived from nitro-aldol reactions of chiral alkoxy aldehydes with a series of nitro compounds. This methodology is utilized in a short and efficient synthesis of the delta-lactone moiety of the HMG-CoA reductase inhibitors compactin and mevinolin.
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