Approaches to the synthesis of cytochalasans. Part 6. Synthesis of the C(14)–C(23) subunit of cytochalasins A,B. F and desoxaphomin |
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Authors: | Jean Ackermann Nada Waespe-ar
evic Christoph Tamm |
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Institution: | Jean Ackermann,Nada Waespe-Šarčevic̀,Christoph Tamm |
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Abstract: | The synthesis of methyl (4R, 8R,)-10-bromo-8-methyl-4-(1,3,6-trioxaheptane)-2-deceneoate ( 5 ), a synthon for the construction of the macrocyclic moieties of the cytochalasins A ( 1), B. (2) F (3) and desoxaphomin ( 4 ) is described. (S)-Glutamic acid ( 6 ) was transformed to the C5-epoxide 10 and 3-methylglutaric acid ( 11 ) to the C5-bromide 15 . Coupling of both 10 and 15 by a CuI-catalyzed Grignard reaction gave the decanol 16 in very high yield. The latter was transformed by several steps to synthon 5 . |
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