Total Synthesis of the Nonadjacent Bis-Tetrahydrofuran Annonaceous Acetogenin Squamostatin-D
β Scribed by Marshall, James A.; Jiang, Hongjian
- Book ID
- 111977932
- Publisher
- American Chemical Society
- Year
- 1998
- Tongue
- English
- Weight
- 92 KB
- Volume
- 63
- Category
- Article
- ISSN
- 0022-3263
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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-
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 ch