Stereocontrolled intramolecular cyclization of ω-tributylstannyl ether aldehydes. synthesis of the 6·7·7·6 ring system of polycyclic ethers

Yoshinori Yamamoto; Jun ichi Yamada; Isao Kadota

doi:10.1016/0040-4039(91)85042-4

Stereocontrolled intramolecular cyclization of ω-tributylstannyl ether aldehydes. synthesis of the 6·7·7·6 ring system of polycyclic ethers

Yoshinori Yamamoto, Jun ichi Yamada, Isao Kadota

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

The BF₃.OEt₂ mediated intramolecular cyclization of the γ-oxo-substituted allylic tin (1) having an aldehyde group at the terminus of the carbon chain proceeded in a stereocontrolled manner to give the 7-membered β-hydroxy cyclic ether (2a) with high diastereoselectivity. This method was applied for the synthesis of the 6·7·7·6 ring system (3a).

Original language	English
Pages (from-to)	7069-7072
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	48
DOIs	https://doi.org/10.1016/0040-4039(91)85042-4
Publication status	Published - Nov 25 1991
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4039(91)85042-4

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title = "Stereocontrolled intramolecular cyclization of ω-tributylstannyl ether aldehydes. synthesis of the 6·7·7·6 ring system of polycyclic ethers",

abstract = "The BF3.OEt2 mediated intramolecular cyclization of the γ-oxo-substituted allylic tin (1) having an aldehyde group at the terminus of the carbon chain proceeded in a stereocontrolled manner to give the 7-membered β-hydroxy cyclic ether (2a) with high diastereoselectivity. This method was applied for the synthesis of the 6·7·7·6 ring system (3a).",

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

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T1 - Stereocontrolled intramolecular cyclization of ω-tributylstannyl ether aldehydes. synthesis of the 6·7·7·6 ring system of polycyclic ethers

AU - Yamamoto, Yoshinori

AU - Yamada, Jun ichi

AU - Kadota, Isao

PY - 1991/11/25

Y1 - 1991/11/25

N2 - The BF3.OEt2 mediated intramolecular cyclization of the γ-oxo-substituted allylic tin (1) having an aldehyde group at the terminus of the carbon chain proceeded in a stereocontrolled manner to give the 7-membered β-hydroxy cyclic ether (2a) with high diastereoselectivity. This method was applied for the synthesis of the 6·7·7·6 ring system (3a).

AB - The BF3.OEt2 mediated intramolecular cyclization of the γ-oxo-substituted allylic tin (1) having an aldehyde group at the terminus of the carbon chain proceeded in a stereocontrolled manner to give the 7-membered β-hydroxy cyclic ether (2a) with high diastereoselectivity. This method was applied for the synthesis of the 6·7·7·6 ring system (3a).

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U2 - 10.1016/0040-4039(91)85042-4

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 48

ER -

Stereocontrolled intramolecular cyclization of ω-tributylstannyl ether aldehydes. synthesis of the 6·7·7·6 ring system of polycyclic ethers

Abstract

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