A convergent enantioselective total synthesis of (−)-perhydrohistrionicotoxin with an intramolecular imino ene-type reaction as a key step
D Tanner, L Hagberg
Index: Tanner, David; Hagberg, Lars Tetrahedron, 1998 , vol. 54, # 27 p. 7907 - 7918
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Citation Number: 37
Abstract
A convergent enantioselective total synthesis of the neurotoxic spirocyclic alkaloid (−)- perhydrohistrionicotoxin (2) is described. A Lewis acid-mediated intramolecular imine ene- type reaction was used for the key spirocyclisation step (14 to 3, with 3 being obtained as a single diastereoisomer). Spirocyclisation precursor 14 was prepared from enantiomerically pure ketone 13, itself available via an efficient one-pot, three-component, coupling ...
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