A rearrangement-cycloaddition approach to spiro-fused indanones

作者：Goldring William P D^*; Bouazzaoui Samira; Malone John F

来源：Tetrahedron Letters, 2011, 52(9): 960-963.

DOI：10.1016/j.tetlet.2010.12.086

• Coleophomone
• Diels-Alder cycloaddition
• Rearrangement
• Indanone
• Spiro-fused ring system

Spiro-fused indanones were constructed using a [4 + 2]-cycloaddition approach from alpha-methylene indanone dienophiles, which were elaborated from 4-chromanone in a number of steps including a key rearrangement process. This type of spiro-fused structure forms the central core ring system found in natural products such as coleophomone A. The cycloaddition reactions using an alpha-methylene indanone dienophile led to the exo diastereoisomer as the major cycloadduct, whereas the 1,4-dione based dienophile predominantly led to the endo diastereoisomer.

• 出版日期2011-3-2