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Stereocontrolled synthesis of the tetrahydrofuran unit of annonaceous acetogenins

โœ Scribed by Keqiang Li; Shikha Vig; Fatih.M. Uckun

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
183 KB
Volume
39
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The THF-epoxide 8 has been prepared from benzyl (R)-(-l-glycidyl ether using a 10-step synthetic scheme in a stereocontrolled fashion. Compound 8 is a highly useful synthon for the synthesis of mono-and di-THF acetogenins. This new synthetic approach can also be applied to the generation of large chemical libraries of acetogenins.

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โœ Lรฉnaรฏck Lemรฉe; Anne Jรฉgou; Alain Veyriรจres ๐Ÿ“‚ Article ๐Ÿ“… 1999 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 252 KB

Iodoeyclisation of 6-O-pivaloyl-D-galaetal followed by radical reduction at C-2 and SN 2 conversion to a 3-endo iodide gave in good yield a [2.2.1] bicyclic acetal which can be regioselectively opened by C-nucleophiles (aUyl silane or silyloxyfuran) in the presence of a Lewis acid to give 2,5-trans-