Synthesis of All Low-Energy Stereoisomers of the Tris(pyrrolidinoindoline) Alkaloid Hodgkinsine and Preliminary Assessment of Their Antinociceptive Activity

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• 作者：Jeremy J. Kodanko ; Sheldon Hiebert ; Emily A. Peterson ; Leonard Sung ; Larry E. Overman ; Viviane de Moura Linck ; Greice Catrine Goerck ; T&acirc ; nia Alves Amador ; Mirna Bainy Leal ; Elaine Elisabetsky
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：October 12, 2007
• 年：2007
• 卷：72
• 期：21
• 页码：7909 - 7914
• 全文大小：113K
• 年卷期：v.72,no.21(October 12, 2007)
• ISSN：1520-6904

文摘

The previously unknown stereoisomers 3, 4, ent-1, and ent-4 of the tris(pyrrolidinoindoline) alkaloidshodgkinsine (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 evaluationof these hodgkinsine stereoisomers in the tail flick and capsaicin pain models are reported.