Synthetic strategies of marine polycyclic ethers via intramolecular allylations

Linear and convergent approaches

Isao Kadota, Yoshinori Yamamoto

Research output: Contribution to journalArticle

70 Citations (Scopus)

Abstract

Strategies for the synthesis of polycyclic ethers based on intramolecular allylations are overviewed. The intramolecular condensation of allylic stannanes and aldehydes is a powerful tool for the synthesis of oxepane derivatives. The reaction is successfully applied to the iterative total synthesis of hemibrevetoxin B (2). Further, the intramolecular allylation of α-acetoxy ethers provides an efficient method for the convergent synthesis of polycyclic ethers. The usefulness of the latter strategy is demonstrated in the convergent total synthesis of gambierol (4).

Original languageEnglish
Pages (from-to)423-432
Number of pages10
JournalAccounts of Chemical Research
Volume38
Issue number5
DOIs
Publication statusPublished - May 2005
Externally publishedYes

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Allylation
Ethers
Aldehydes
Condensation
Derivatives

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthetic strategies of marine polycyclic ethers via intramolecular allylations : Linear and convergent approaches. / Kadota, Isao; Yamamoto, Yoshinori.

In: Accounts of Chemical Research, Vol. 38, No. 5, 05.2005, p. 423-432.

Research output: Contribution to journalArticle

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