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A novel and general approach for synthesis of the multi-oxygenated dihydrofuran sesquiterpenes has been de-veloped starting from santonin. The key steps involve: the strategic acid-catalyzed double-bond shifting affording 4, the novel base-promoted epoxide rearrangement of 5 generating two key functionals (the C5-OH and the D7,11 dou-ble bond), and the stereoselective cyclization of tetrahydrofuran ring without pre-controlling the stereochemistry of C-7. As an example of this approach, synthesis of (+)-2,14-deoxyalatol was described in detail.
A novel and general approach for synthesis of the multi-oxygenated dihydrofuran sesquiterpenes has been de-veloped starting from santonin. The key steps involve: the strategic acid-catalyzed double-bond shifting affording 4, the novel base-promoted epoxide rearrangement of 5 generating two the key functionals (the C5-OH and the D7,11 dou-ble bond), and the stereoselective cyclization of the tetrahydrofuran ring without pre-controlling the stereochemistry of C-7. As an example of this approach, synthesis of (+) - 2,14-deoxyalatol was described in detail.