A New Approach to the Construction of β-Alkoxy-Substituted Cyclic Ethers via the Intramolecular Cyclization of ω-Trialkylplumbyl and w-Trialkylstannyl Ether Acetals

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

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

: The w-trialkylplumbyl ether acetal (la) gave the β-alkoxy cyclic ether (2a) upon treatment with 2 equiv of TiCl4in CH2C12. The reaction of the ω-trialkylstannyl ether acetals 3, 4, and 5 in the presence of 2 equiv of TiCl3 (OiPr) in CH2C12 produced the corresponding 0-alkoxy- a-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
DOIs
Publication statusPublished - Jan 1 1990
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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