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New reactions and step economy: the total synthesis of (±)-salsolene oxide based on the type II transition metal-catalyzed intramolecular [4+4] cycloaddition

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
62
Issue
32
Identifiers
DOI: 10.1016/j.tet.2006.02.085
Disciplines
  • Economics
  • Mathematics

Abstract

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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