What is it about?
(Z)-Enediynes are reactive molecules that undergo Bergman cycloaromatization to generate diradical species. This unique reactivity is responsible for the remarkable DNA-cleaving ability and potent antitumor activity of naturally occurring enediyne antibiotics. In this study, we developed a new consecutive reaction of 1-chlorovinyl p-tolyl sulfoxides with lithium acetylides that efficiently produces a variety of (Z)-enediynes with excellent stereoselectivity. Mechanistic studies using isotope-labeled substrates also revealed an unexpected reaction pathway involving β-C–H bond cleavage.
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Why is it important?
The biological activity and unique reactivity of enediynes make stereoselective access to (Z)-enediynes highly desirable. However, existing methods often require stereochemically pure starting materials or provide limited control of alkene geometry. Our method directly furnishes (Z)-enediynes with high stereoselectivity through an unexpected consecutive reaction, offering a practical new route to these valuable molecular frameworks.
Perspectives
This work uncovers a previously unknown reaction of 1-chlorovinyl p-tolyl sulfoxides and expands their synthetic utility. Because (Z)-enediynes are important structural motifs, this stereoselective strategy may facilitate the preparation of new enediyne-based compounds and inspire further reaction development.
Associate Professor Tsutomu Kimura
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This page is a summary of: A novel consecutive reaction of lithium acetylides with 2-aryl-1-chlorovinyl p-tolyl sulfoxides leading to the formation of (Z)-enediynes, Tetrahedron Letters, February 2013, Elsevier,
DOI: 10.1016/j.tetlet.2012.11.152.
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