Synthesis of all low-energy stereoisomers of the tris(pyrrolidinoindoline) alkaloid hodgkinsine and preliminary assessment of their antinociceptive activity |
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Authors: | Kodanko Jeremy J Hiebert Sheldon Peterson Emily A Sung Leonard Overman Larry E de Moura Linck Viviane Goerck Greice Catrine Amador Tânia Alves Leal Mirna Bainy Elisabetsky Elaine |
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Affiliation: | Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA. |
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Abstract: | The previously unknown stereoisomers 3, 4, ent-1, and ent-4 of the tris(pyrrolidinoindoline) alkaloids hodgkinsine (1) and hodgkinsine B (2) were prepared by stereocontrolled total synthesis. In each synthesis, a catalyst-controlled intramolecular Heck reaction was the key step in appending a third cis-pyrrolidinoindoline ring to a hexacyclic chimonanthine precursor. Results of the preliminary evaluation of these hodgkinsine stereoisomers in the tail flick and capsaicin pain models are reported. |
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