Total syntheses of (+)- and (-)-pestalotiopsin A

Ken Ichi Takao, Nobuhiko Hayakawa, Reo Yamada, Taro Yamaguchi, Hiroshi Saegusa, Masatoshi Uchida, Suguru Samejima, Kin Ichi Tadano

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(Chemical Equation Presented) An enantioselective total synthesis of both enantiomers of caryophyllene-type sesquiterpenoid pestalotiopsin A has been achieved, thereby establishing the absolute stereochemistry of natural (+)-pestalotiopsin A. Highlights of the synthesis include a [2 + 2] cycloaddition of N-propioloyl Oppolzer's camphorsultam and ketene dialkyl acetal and subsequent highly stereoselective 1,4-hydride addition/protonation, an aldol reaction of functionalized bicyclic lactone with aldehyde, an efficient intramolecular Nozaki-Hiyama-Kishi (NHK) reaction for the construction of the highly strained (E)-cyclononene ring, and a palladium-catalyzed reduction of allylic mesylate with retention of the E configuration.

Original languageEnglish
Pages (from-to)6452-6461
Number of pages10
JournalJournal of Organic Chemistry
Issue number17
Publication statusPublished - 2009 Sep 4

ASJC Scopus subject areas

  • Organic Chemistry

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    Takao, K. I., Hayakawa, N., Yamada, R., Yamaguchi, T., Saegusa, H., Uchida, M., Samejima, S., & Tadano, K. I. (2009). Total syntheses of (+)- and (-)-pestalotiopsin A. Journal of Organic Chemistry, 74(17), 6452-6461.