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

• DOI: 10.1016/j.tet.2011.11.063
• Publication Date: 2011-12-02T08:47:33Z
• Authors: Hang Cheng; Liang Xu; De-Lin Chen; Qiao-Hong Chen; Feng-Peng Wang
• Keywords: Diels–Alder reaction; Intramolecular reaction

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.