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.

Additional Information

Publication
Tetrahedron 2006, 62, 7505-7511.
Language: English
Date: 2006
Keywords
Chemical reactions, Organic synthesis, Reaction efficiency