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Literature DB >> 24273444

A Concise Synthesis of R-(-)-Cicutoxin, a Natural 17-Carbon Polyenyne.

Abstract

A concise synthesis of the natural polyenyne R-(-)-cicutoxin (1) is described. After several trials, the successful synthesis commenced with three key fragments, R-(-)-1-hexyn-3-ol (8), 1,4-diiodo-1,3-butadiene (9), and the THP protected 4,6-heptadiyn-1-ol (6). Sonogashira coupling of compound 9 with acetylenes 6 and 8 gave the 17-carbon frame, which upon regio-selective reduction of a triple bond with red Al and removal of the THP protecting group afforded the natural product in four linear steps. The triply convergent synthesis gave R-(-)-cicutoxin in 18% overall yield.

Entities: Chemical Disease Species

Keywords: Total synthesis; antileukemic; cicutoxin; natural product

Year: 2009 PMID： 24273444 PMCID： PMC3835075 DOI： 10.1002/ejoc.200801172

Source DB: PubMed Journal: European J Org Chem ISSN： 1099-0690

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9 in total

A Concise Synthesis of R-(-)-Cicutoxin, a Natural 17-Carbon Polyenyne.

1. Catalytic asymmetric synthesis of allylic aryl ethers.

2. First Total Synthesis of the Potent Anticancer Natural Product Dideoxypetrosynol A: Preparation of the "Skipped" (Z)-Enediyne Moiety by Oxidative Coupling of Homopropargyl Phosphonium Ylide.

3. A fatal case of apparent water hemlock poisoning.

4. Antitumor agents, 85. Cicutoxin, an antileukemic principle from Cicuta maculata, and the cytotoxicity of the related derivatives.

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9. Total synthesis of (+)- and (-)-duryne: a potent anticancer agent from the marine sponge Cribrochalina dura. Establishment of the central double bond geometry and the absolute configuration of the chiral centers.