Synthesis of (±)-Marasmic Acid via 1-Oxaspirohexane Rearrangement

Yoshito Tobe*, Dai Yamashita, Tohru Takahashi, Masashi Inata, Jun ichi Sato, Kiyomi Kakiuchi, Kazuya Kobiro, Yoshinobu Odaira

*此作品的通信作者

研究成果: Article同行評審

37 引文 斯高帕斯(Scopus)

摘要

A formal total synthesis of marasmic acid (1), an antimicrobial sesquiterpene, has been achieved in a stereoselective manner from known enone 9. The initial key step involves stereo-and regioselective photocycloaddition of aliene to enone 8. The most important strategic transformation in this synthesis is the acid-catalyzed rearrangement of 1-oxaspirohexane 7 to lactone 6 having a norcarane skeleton with an appendage suitable for further manipulation. Finally, Sharpless allylic oxidation followed by Swern oxidation of hydroxy ester 24 provided a route to methyl marasmate (5).

原文English
頁(從 - 到)775-779
頁數5
期刊Journal of the American Chemical Society
112
發行號2
DOIs
出版狀態Published - 1 1月 1990

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