Abstract
Five-membered ring lactones abound in nature and have ever since challenged synthetic chemists.1,3 They comprise butanolides (1), butenolides (2), α-alkylidenebutanolides (3), and γ-alkylidenebutenolides (4; Fig. 1). We have developed versatile routes to such compounds. They encompass only a few steps and ensure a high degree of stereocontrol at all stereogenic sp 3 centers and C=C bonds. In addition they allow to vary the substituents R, R′, and R″ considerably. Therefore, we were able to synthesize butanolides and butenolides which differed structurally from one another distinctly.
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References
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Harcken, C. et al. (1999). Stereoselective Syntheses of γ-Lactones and γ-Alkylidene- Butenolides. In: Scolastico, C., Nicotra, F. (eds) Current Trends in Organic Synthesis. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-4801-0_19
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DOI: https://doi.org/10.1007/978-1-4615-4801-0_19
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