A new approach to the construction of β-alkoxy-substituted cyclic ethers via the intramolecular cyclization of ω-trialkylplumbyl and ω-trialkylstannyl ether acetals

Jun Ichi Yamada, Tetsuya Asano, Isao Kadota, Yoshinori Yamamoto

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52 Citations (Scopus)

Abstract

The ω-trialkylplumbyl ether acetal (1a) gave the β-alkoxy cyclic ether (2a) upon treatment with 2 equiv of TiCl4 in CH2Cl2. The reaction of the ω-trialkylstannyl ether acetals 3, 4, and 5 in the presence of 2 equiv of TiCl3 (OiPr) in CH2Cl2 produced the corresponding β-alkoxy-α-vinyl cyclic ethers 6, 7, and 8, respectively. This new procedure permitted the chiral synthesis of a fundamental structural unit (20) of cyclic ether natural products.

Original languageEnglish
Pages (from-to)6066-6068
Number of pages3
JournalJournal of Organic Chemistry
Volume55
Issue number25
Publication statusPublished - 1990
Externally publishedYes

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Cyclic Ethers
Acetals
Cyclization
Ether
Biological Products
alkoxyl radical

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

A new approach to the construction of β-alkoxy-substituted cyclic ethers via the intramolecular cyclization of ω-trialkylplumbyl and ω-trialkylstannyl ether acetals. / Yamada, Jun Ichi; Asano, Tetsuya; Kadota, Isao; Yamamoto, Yoshinori.

In: Journal of Organic Chemistry, Vol. 55, No. 25, 1990, p. 6066-6068.

Research output: Contribution to journalArticle

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AU - Yamada, Jun Ichi

AU - Asano, Tetsuya

AU - Kadota, Isao

AU - Yamamoto, Yoshinori

PY - 1990

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