The second generation synthesis of (+)-pseudodeflectusin |
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| Authors: | Yuna SatoKouji Kuramochi Takahiro SuzukiAtsuo Nakazaki Susumu Kobayashi |
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| Affiliation: | a Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI), 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan
b Department of Applied Biological Sciences, Faculty of Science and Technology, Tokyo University of Science (RIKADAI), 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan |
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| Abstract: | The second generation synthesis of (+)-pseudodeflectusin (1), a potential antitumor agent, has been achieved. The key synthetic step is the cascade reaction involving Diels-Alder reaction, lactonization, and decarboxylation to give cycloadduct 6 with complete regioselectivity in good yield. We found that NaH is the best base to facilitate the Diels-Alder reaction of hydroxypyrone 7 with alkyne 8. The present synthetic route enables the total synthesis of (+)-1 in only five-steps from the known compounds 7 and 8. |
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| Keywords: | Regioselective Diels-Alder reaction Cascade reaction Formal total synthesis (+)-Pseudodeflectusin Antitumor activity |
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