Journal
SYNTHESIS-STUTTGART
Volume 48, Issue 12, Pages 1892-1901Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0035-1561590
Keywords
cyclopropanes; benzofurans; natural products; ring opening; cyclization; total synthesis
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Funding
- Japan Society for the Promotion of Science (JSPS) [15K07853]
- Grants-in-Aid for Scientific Research [15K07853] Funding Source: KAKEN
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Acid-catalyzed ring-opening cyclization of cyclohexane-1,3-dione-2-spirocyclopropanes under metal-free conditions proceeded smoothly at room temperature to provide 2-aryl-3,5,6,7-tetrahydro-1-benzofuran-4(2H)-ones in excellent yields without the formation of 3-substituted isomers. The obtained product was converted into a 2-arylbenzofuran derivative via a synthetically useful 2-aryl-2,3-dihydrobenzofuran intermediate. Furthermore, the first total synthesis of cuspidan B was achieved by using the present method.
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