Journal of the Chemical Society. Perkin transactions I p. 1557 - 1562 (1981)
Update date:2022-08-05
Topics:
Tokoroyama, Takashi
Fukuyama, Yoshiyasu
Kubota, Takashi
Yokotani, Kenji
The total synthesis of fraxinellone (1), the simplest example of degraded limonoid, via the 6-formyl-2,6-dimethylcyclohex-2-enecarboxylates (2) is described.In the initial approach the C-6 methylation of ethyl 6-formyl-2-methylcyclohex-2-enecarboxylate (7) was carried out by cyclopropanation and ring cleavage which unexpectedly gave the bicyclo<2.2.1>heptane compound (20), with a poor yield of the desired product.Subsequently, the key intermediate (2) was synthesized effectively by the Diels-Alder reaction between ethyl 3-methylpenta-2,4-dienoate and methacrolein.The reaction of the aldehyde ester (2) with furyl-lithium followed by double-bond isomerization with base afforded (+/-)-fraxinellone, together with the corresponding diastereoisomer.
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