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An expedient synthesis of 2,5-disubstituted-3-oxygenated tetrahydrofurans

✍ Scribed by Caroline L. Nesbitt; Christopher S.P. McErlean

Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
351 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

Single enantiomer 2,5-disubstituted-3-oxygenated tetrahydrofurans are synthesized in as little as four steps from a commercially available epoxide. The key steps are homoallylic alcohol epoxidation, palladium-catalysed alkoxy-carbonylation-lactonisation and Mitsunobu inversion. The protocol is applied to the formal total syntheses of (+)-kumausallene, (6S,7S,9R,10R)-6,9-epoxynonadec-18-ene-7,10-diol and the core of lytophilippine A.

πŸ“œ SIMILAR VOLUMES

A stereocontrolled synthesis of anti-2,5
A stereocontrolled synthesis of anti-2,5-disubstituted tetrahydrofurans
✍ Sung Ho Kang; Sung Bae Lee πŸ“‚ Article πŸ“… 1993 πŸ› Elsevier Science 🌐 French βš– 291 KB

AxG2,Sdisubstitutad tetrahydrofurans, in which one of the subetituents is 3'-furany group, have been derived from trans-4(3'-furanyl)\_3-butenols 3-g by using iodine in diethyl ether in the presence of potassium carbonate at -78Β°C.