A new approach to the synthesis of cyclic ethers via the intermolecular allylation of α-acetoxy ethers and ring-closing metathesis

Isao Kadota, Hiroshi Uyehara, Yoshinori Yamamoto

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

A concise synthesis of the isolaurepinnacin skeleton 6 was achieved via the intermolecular allylation of the α-acetoxy ether 3 followed by ring-closing metathesis. This methodology was successfully applied to the convergent synthesis of the oxocene 15, an advanced synthetic intermediate for the total synthesis of laurencin.

Original languageEnglish
Pages (from-to)7361-7365
Number of pages5
JournalTetrahedron
Volume60
Issue number34
DOIs
Publication statusPublished - Aug 16 2004
Externally publishedYes

Fingerprint

Cyclic Ethers
Allylation
Ethers
Skeleton
Ether
isolaurepinnacin
laurencin

Keywords

  • Allylation
  • Lewis acid
  • Marine natural product
  • Polycyclic ether
  • RCM

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A new approach to the synthesis of cyclic ethers via the intermolecular allylation of α-acetoxy ethers and ring-closing metathesis. / Kadota, Isao; Uyehara, Hiroshi; Yamamoto, Yoshinori.

In: Tetrahedron, Vol. 60, No. 34, 16.08.2004, p. 7361-7365.

Research output: Contribution to journalArticle

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