期刊
SYNLETT
卷 -, 期 7, 页码 1144-1148出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0028-1088152
关键词
lactones; aldehydes; oxidations; drugs; statins
(4R,6S)-4-(tert-Butyldimethylsilyloxy)-6-formyltetrahydro-2H-pyran-2-one has been prepared for the first time by oxidation of alcohol (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one. The oxidation of the alcohol was performed with Dess-Martin periodinane in up to 95% yield. Because of limited stability of the aldehyde, it was isolated in the form of hydrate for isolation and storage purposes. The latter can be dehydrated back to the aldehyde quantitatively by simple dissolution in an apolar organic solvent followed by removal of volatiles. The aldehyde was demonstrated to undergo Wittig olefination in high yield. Presented findings set a key platform for statin synthesis via lactonized side chain.
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