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

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)3831-3842
Number of pages12
JournalJournal of Organic Chemistry
Volume75
Issue number11
DOIs
Publication statusPublished - 2010 Jun 4
Externally publishedYes

Fingerprint

Carbonates
Cyclization
Palladium
Chlorides
Bearings (structural)
Nucleophiles
Biological Products
pachastrissamine
benzamide

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Ring-construction/stereoselective functionalization cascade : Total synthesis of pachastrissamine (Jaspine B) through palladium-catalyzed bis-cyclization of propargyl chlorides and carbonates. / Inuki, Shinsuke; Yoshimitsu, Yuji; Oishi, Shinya; Fujii, Nobutaka; Ohno, Hiroaki.

In: Journal of Organic Chemistry, Vol. 75, No. 11, 04.06.2010, p. 3831-3842.

Research output: Contribution to journalArticle

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AU - Ohno, Hiroaki

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