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

*Corresponding author for this work

Research output: Contribution to journalArticle

33 Scopus citations

Abstract

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).

Original languageEnglish
Pages (from-to)775-779
Number of pages5
JournalJournal of the American Chemical Society
Volume112
Issue number2
DOIs
StatePublished - 1 Jan 1990

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    Tobe, Y., Yamashita, D., Takahashi, T., Inata, M., Sato, J. I., Kakiuchi, K., Kobiro, K., & Odaira, Y. (1990). Synthesis of (±)-Marasmic Acid via 1-Oxaspirohexane Rearrangement. Journal of the American Chemical Society, 112(2), 775-779. https://doi.org/10.1021/ja00158a042