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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Authors: | Paul A Wender Mitchell P Croatt |
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Institution: | a Department of Chemistry, Stanford University, Stanford, CA 94305, USA b Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweb 10-14, 55099 Mainz, Germany |
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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. |
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