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1. Construction of functionalized B/C/D ring system of C19-diterpenoid alkaloids via intramolecular Diels–Alder reaction followed by Wagner–Meerwein rearrangement

Author

Cheng, Hang, Xu, Liang, Chen, De-Lin, Chen, Qiao-Hong, and Wang, Feng-Peng

Subjects
*ALKALOIDS, *DITERPENES, *DIELS-Alder reaction, *REARRANGEMENTS (Chemistry), *BENZOQUINONES, *FUNCTIONAL groups, *PHASE transitions
Abstract

Abstract: A concise strategy for construction of B/C/D ring system of C19-diterpenoid alkaloids was described, which features a highly diastereoselective intramolecular Diels–Alder reaction of masked o-benzoquinone and an efficient Wagner–Meerwein 1,2-shift rearrangement. The functional group transformations of rearrangement product 19 demonstrate a potential for stereoselective installation of oxygen functions on D-ring of many type of C19-diterpenoid alkaloids. [Copyright &y& Elsevier]

Published
2012
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