Total Synthesis of Pulvomycin D |
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Authors: | Lukas Fritz Dr Sebastian Wienhold Sabrina Hackl Prof?Dr Thorsten Bach |
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Institution: | School of Natural Sciences, Department of Chemistry and Catalysis Research Center, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching, Germany |
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Abstract: | A synthetic route to the pulvomycin class of natural products is presented, which culminated in the first synthesis of a pulvomycin, pulvomycin D. Key elements of the strategy include a pivotal aldol reaction which led to bond formation between the C24-C40 and the C8-C23 fragment. The remaining C1-C7 fragment was attached by a Yamaguchi esterification completing the assembly of the 40 carbon atoms within the main skeleton. Ring closure to the 22-membered lactone ring was achieved in the final stages of the synthesis by a Heck reaction. The completion of the synthesis required the removal of six silyl protecting groups in combination with olefin formation at C26-C27 by a Peterson elimination. |
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Keywords: | aldol reactions Heck reactions protecting groups polyketides total synthesis |
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