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

doi:10.1021/jo00312a003

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 journal › Article › peer-review

12 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 language	English
Pages (from-to)	6066-6068
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	55
Issue number	25
DOIs	https://doi.org/10.1021/jo00312a003
Publication status	Published - 1990
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo00312a003

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

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.",

author = "Yamada, {Jun ichi} and Tetsuya Asano and Isao Kadota and Yoshinori Yamamoto",

year = "1990",

doi = "10.1021/jo00312a003",

language = "English",

volume = "55",

pages = "6066--6068",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "25",

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TY - JOUR

T1 - A New Approach to the Construction of β-Alkoxy-Substituted Cyclic Ethers via the Intramolecular Cyclization of ω-Trialkylplumbyl and w-Trialkylstannyl Ether Acetals

AU - Yamada, Jun ichi

AU - Asano, Tetsuya

AU - Kadota, Isao

AU - Yamamoto, Yoshinori

PY - 1990

Y1 - 1990

N2 - : 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.

AB - : 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.

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U2 - 10.1021/jo00312a003

DO - 10.1021/jo00312a003

M3 - Article

AN - SCOPUS:33751554168

SN - 0022-3263

VL - 55

SP - 6066

EP - 6068

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 25

ER -

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

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