Synthesis of 6/6/6-tricyclic ether system via Achmatowicz and intramolecular oxa-michael reactions

Hiroki Yamamoto; Kohei Torikai; Makoto Ebine; Tohru Oishi

doi:10.3987/COM-17-S(T)10

Synthesis of 6/6/6-tricyclic ether system via Achmatowicz and intramolecular oxa-michael reactions

Hiroki Yamamoto, Kohei Torikai, Makoto Ebine, Tohru Oishi

Organic and Biological Chemistry

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

4 Citations (Scopus)

Abstract

Synthesis of 6/6/6-tricyclic ethers possessing 1,3-diaxial methyl groups was examined via Achmatowicz reaction and intramolecular oxa-Michael reaction. A key precursor was prepared via coupling of an aldehyde with a furyllithium derivative followed by radical deoxygenation of the resulting secondary alcohol. The intramolecular oxa-Michael reaction proceeded in a stereoselective manner to afford cis-fused product as a single isomer.

Original language	English
Pages (from-to)	158-162
Number of pages	5
Journal	Heterocycles
Volume	97
Issue number	1
DOIs	https://doi.org/10.3987/COM-17-S(T)10
Publication status	Published - 2018

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Pharmacology
Organic Chemistry

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10.3987/COM-17-S(T)10

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title = "Synthesis of 6/6/6-tricyclic ether system via Achmatowicz and intramolecular oxa-michael reactions",

abstract = "Synthesis of 6/6/6-tricyclic ethers possessing 1,3-diaxial methyl groups was examined via Achmatowicz reaction and intramolecular oxa-Michael reaction. A key precursor was prepared via coupling of an aldehyde with a furyllithium derivative followed by radical deoxygenation of the resulting secondary alcohol. The intramolecular oxa-Michael reaction proceeded in a stereoselective manner to afford cis-fused product as a single isomer.",

author = "Hiroki Yamamoto and Kohei Torikai and Makoto Ebine and Tohru Oishi",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Numbers JP24245009, JP16H04112, and Funding Information: This work was supported by JSPS KAKENHI Grant Numbers JP24245009, JP16H04112, and JP16H01159 in Middle Molecular Strategy, and the Asahi Glass Foundation.",

year = "2018",

doi = "10.3987/COM-17-S(T)10",

language = "English",

volume = "97",

pages = "158--162",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "1",

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TY - JOUR

T1 - Synthesis of 6/6/6-tricyclic ether system via Achmatowicz and intramolecular oxa-michael reactions

AU - Yamamoto, Hiroki

AU - Torikai, Kohei

AU - Ebine, Makoto

AU - Oishi, Tohru

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Numbers JP24245009, JP16H04112, and Funding Information: This work was supported by JSPS KAKENHI Grant Numbers JP24245009, JP16H04112, and JP16H01159 in Middle Molecular Strategy, and the Asahi Glass Foundation.

PY - 2018

Y1 - 2018

N2 - Synthesis of 6/6/6-tricyclic ethers possessing 1,3-diaxial methyl groups was examined via Achmatowicz reaction and intramolecular oxa-Michael reaction. A key precursor was prepared via coupling of an aldehyde with a furyllithium derivative followed by radical deoxygenation of the resulting secondary alcohol. The intramolecular oxa-Michael reaction proceeded in a stereoselective manner to afford cis-fused product as a single isomer.

AB - Synthesis of 6/6/6-tricyclic ethers possessing 1,3-diaxial methyl groups was examined via Achmatowicz reaction and intramolecular oxa-Michael reaction. A key precursor was prepared via coupling of an aldehyde with a furyllithium derivative followed by radical deoxygenation of the resulting secondary alcohol. The intramolecular oxa-Michael reaction proceeded in a stereoselective manner to afford cis-fused product as a single isomer.

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JO - Heterocycles

JF - Heterocycles

IS - 1

ER -

Synthesis of 6/6/6-tricyclic ether system via Achmatowicz and intramolecular oxa-michael reactions

Abstract

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