Enantioselective synthesis of the nagilactone ring system via vinylsilane-mediated polyene cyclization
โ Scribed by Steven D. Burke; Sharon M.S. Strickland; Helen M. Organ; Louis A. Silks III
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 238 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
The functionalized tricyclic nagilactone precursor 19 was synthesized by a route featuring a vinylsilane terminated/1,3-dioxane acetal initiated bicyclization. Relative and absolute stereochemical control were achieved via the optically active pentenolide template 14.
๐ SIMILAR VOLUMES
The c~-diazoester I in the presence of catalytic Rh2(OAc)4 was converted to the carbapenam 2. The synthesis of 1 and a proposed mechanism are described. A variety of strategies currently exists in the literature for the synthesis of bicyclic 13-1actams.
The cross conjugated 13-keto ester system was found to be an excellent promoter for polyene cyclization involving a thiophene ring to facilitate the synthesis of polycyclic thiophene-containing compounds.