Stereoselective total synthesis of muconin |
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| Authors: | Shunya Takahashi Akemi KubotaTadashi Nakata |
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| Affiliation: | a RIKEN (The Institute of Physical and Chemical Research), Hirosawa 2-1, Wako-shi, Saitama 351-0198, Japan
b Graduate School of Science and Engineering, Saitama University, Saitama, Saitama 338-8570, Japan |
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| Abstract: | An antitumor acetogenin, muconin, was synthesized through a coupling reaction of a THF-THP segment and a terminal butenolide. The key reactions include successive ether-ring formation reaction under acidic and basic conditions or one-pot double cyclization promoted by TBAF and stereoselective reduction of acyclic ketones adjacent to the 2,6-cis THP with Zn(BH4)2. |
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| Keywords: | annonaceous acetogenin antitumor agent muconin Zn(BH4)2 reduction |
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