Chemical synthesis study demonstrates a stereoselective Michael-Mannich annelation using indoles and dienes, indicating concise routes to complex polycyclic alkaloids.
A novel annelation strategy has been devised for stereoselective synthesis of tetrahydrocarbazoles. The pathway features a regio- and stereocontrolled condensation of indole and its substituted derivatives with electron-deficient 1,3-dienes via a Michael-Mannich reaction sequence. An extension of this method to include cross-conjugated allenes as substrates also results in a Michael-Mannich-Michael cascade, incorporating 2 equiv of indole with increasing product complexity. The formal 4π + 2π cyclization describes a concise route to polycyclic alkaloids of this family.
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Williams et al. (2017) studied this question.
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