期刊
TETRAHEDRON LETTERS
卷 52, 期 5, 页码 626-629出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.11.153
关键词
Regioselective Diels-Alder reaction; Cascade reaction; Formal total synthesis; (+)-Pseudodeflectusin; Antitumor activity
资金
- Japan Society for the Promotion of Science [22390004]
- Grants-in-Aid for Scientific Research [22390004] Funding Source: KAKEN
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. (C) 2010 Elsevier Ltd. All rights reserved.
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