Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C |
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Authors: | Shoji Kobayashi Shin-ichiro Tanaka |
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Institution: | Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan |
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Abstract: | The ABCDE ring moiety of ciguatoxin CTX3C, a major causative agent of ciguatera poisoning, was stereoselectively synthesized. The key transformations are a chiral auxiliary-based asymmetric alkylation and an asymmetric aldol condensation, which controlled the formation of the C11 and C21-stereocenters, respectively. A highly practical and efficient route to the ABCD ring fragment, a common precursor for the divergent synthesis of the left wings of ciguatoxins, was also established. |
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Keywords: | Asymmetric alkylation Asymmetric aldol condensation Ring-closing metathesis Ciguatoxin CTX3C |
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