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A rearrangement–cycloaddition approach to spiro-fused indanones

✍ Scribed by William P.D. Goldring; Samira Bouazzaoui; John F. Malone

Publisher
Elsevier Science
Year
2011
Tongue
French
Weight
469 KB
Volume
52
Category
Article
ISSN
0040-4039

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✦ Synopsis

Spiro-fused indanones were constructed using a [4 + 2]-cycloaddition approach from a-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 a-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.

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