First Synthesis of (+)-2,14-Deoxyalatol from α-Santonin
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摘要:
A novel and general approach for synthesis of the multi-oxygenated dihydrofuran sesquiterpenes has been developed 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(7,11 double 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.