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査読

58 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)3831-3842
ページ数12
ジャーナルJournal of Organic Chemistry
75
11
DOI
出版ステータスPublished - 2010 6月 4

ASJC Scopus subject areas

  • 有機化学

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