Ring-construction/stereoselective functionalization cascade: Total synthesis of pachastrissamine (Jaspine B) through palladium-catalyzed bis-cyclization of propargyl chlorides and carbonates

Shinsuke Inuki, Yuji Yoshimitsu, Shinya Oishi, Nobutaka Fujii, Hiroaki Ohno

研究成果: Article

51 引用 (Scopus)

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Figure presented Palladium(0)-catalyzed cyclization of bromoallenes, propargyl chlorides, and carbonates bearing hydroxy and benzamide groups as internal nucleophiles stereoselectively provides functionalized tetrahydrofuran. Cyclization reactivity is dependent on the relative configuration of the benzamide and leaving groups, and on the nature of the leaving groups. This bis-cyclization was used as the key step in a short total synthesis of pachastrissamine, which is a biologically active marine natural product.

元の言語English
ページ(範囲)3831-3842
ページ数12
ジャーナルJournal of Organic Chemistry
75
発行部数11
DOI
出版物ステータスPublished - 2010 6 4
外部発表Yes

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ASJC Scopus subject areas

  • Organic Chemistry

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