Synthesis of the N-acetylcysteamine thioester of seco-proansamitocin |
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Authors: | Frenzel Thomas Brünjes Marco Quitschalle Monika Kirschning Andreas |
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Institution: | Institut für Organische Chemie der Universit?t Hannover, Germany. |
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Abstract: | structure: see text] The enantioselective total synthesis of the N-acetylcysteamine thioester of seco-proansamitocin, a key biosynthetic intermediate of the highly potent antitumor agent ansamitocin, is described, which twice utilizes the Nagao acetate aldol reaction, as well as an indium-mediated alkynylation of a benzyl bromide followed by carboalumination. The key step is a Heck reaction between two terminal alkenes for merging the two major fragments. |
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