Journal article
A Convergent Enantioselective Total Synthesis of (-)-Perhydrohistrionicotoxin with an Intramolecular Imino Ene-type Reaction as a Key Step
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 reaction involving chiral electrophiles 9 and 10.
The stereogenic centres of 9 and 10 derive in turn from Sharpless kinetic resolution, which allowed access to both chiral electrophiles from a common racemic precursor, 8. (C) 1998 Elsevier Science Ltd. All rights reserved.
Language: | English |
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Year: | 1998 |
Pages: | 7907-7918 |
ISSN: | 14645416 and 00404020 |
Types: | Journal article |
DOI: | 10.1016/S0040-4020(98)00425-6 |
ORCIDs: | Tanner, David Ackland |