New reactions and step economy: the total synthesis of (±)-salsolene oxide based on the type II transition metal-catalyzed intramolecular [4 + 4] cycloaddition
- UNCG Author/Contributor (non-UNCG co-authors, if there are any, appear on document)
- Mitchell Croatt, Assistant Professor (Creator)
- Institution
- The University of North Carolina at Greensboro (UNCG )
- Web Site: http://library.uncg.edu/
Abstract: Studies on the viability of the type II nickel-catalyzed intramolecular [4+4] cycloaddition of bis-dienes show that it is influenced by both diene substitution and geometry. Both E- and Z-isomers of 19 and 20 react, albeit at markedly different rates, to afford cycloadducts, whereas only the Z-isomer of 9 (and not the E-isomer) reacts to give 8 and 25. Chemoselective elaboration of 8 to (±)-salsolene oxide (7) was used to confirm the cycloadduct structure while establishing a step economical route to the natural product.
New reactions and step economy: the total synthesis of (±)-salsolene oxide based on the type II transition metal-catalyzed intramolecular [4 + 4] cycloaddition
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Created on 3/10/2011
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Additional Information
- Publication
- Tetrahedron 2006, 62, 7505-7511.
- Language: English
- Date: 2006
- Keywords
- Chemical reactions, Organic synthesis, Reaction efficiency