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An intramolecular [4+3]-cycloaddition approach to rameswaralide inspired by biosynthesis speculation

✍ Scribed by Gerald Pattenden; Johan M. Winne

Publisher: Elsevier Science
Year: 2009
Tongue: French
Weight: 382 KB
Volume: 50
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.10.046

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✦ Synopsis

A concise synthesis of the polycycle 27, which incorporates the 5,5,7-tricyclic ring core of rameswaralide 1, using a biogenetically inspired acid-catalysed [4+3]-cycloaddition approach starting from the furanobutenolide 26 is described, namely, 26?28/29?27. Under thermal conditions, the same furanobutenolide 26 gives the alternative polycyclic compound 35, resulting from a [4+2]-cycloaddition involving the furan as dienophile.

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