Stereocontrolled synthesis of substituted bicyclic ethers through oxy-Favorskii rearrangement: Total synthesis of (±)-communiol e

Shoji Kobayashi; Tatsuhiro Kinoshita; Takuji Kawamoto; Masato Wada; Hiroyuki Kuroda; Araki Masuyama; Ilhyong Ryu

doi:10.1021/jo201064h

Stereocontrolled synthesis of substituted bicyclic ethers through oxy-Favorskii rearrangement: Total synthesis of (±)-communiol e

Shoji Kobayashi^*, Tatsuhiro Kinoshita, Takuji Kawamoto, Masato Wada, Hiroyuki Kuroda, Araki Masuyama, Ilhyong Ryu

^*Corresponding author for this work

Department of Applied Chemistry

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

18 Scopus citations

Abstract

The potential of the oxy-Favorskii rearrangement to form branched cis-fused bicyclic ethers was explored. Both tertiary and quaternary centers were constructed in highly stereospecific manners. Methanol and primary amines were effective nucleophiles for the rearrangement. The total synthesis of (±)-communiol E was achieved based on this method.

Original language	English
Pages (from-to)	7096-7103
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	76
Issue number	17
DOIs	https://doi.org/10.1021/jo201064h
State	Published - 2 Sep 2011

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title = "Stereocontrolled synthesis of substituted bicyclic ethers through oxy-Favorskii rearrangement: Total synthesis of (±)-communiol e",

abstract = "The potential of the oxy-Favorskii rearrangement to form branched cis-fused bicyclic ethers was explored. Both tertiary and quaternary centers were constructed in highly stereospecific manners. Methanol and primary amines were effective nucleophiles for the rearrangement. The total synthesis of (±)-communiol E was achieved based on this method.",

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Stereocontrolled synthesis of substituted bicyclic ethers through oxy-Favorskii rearrangement : Total synthesis of (±)-communiol e. / Kobayashi, Shoji; Kinoshita, Tatsuhiro; Kawamoto, Takuji; Wada, Masato; Kuroda, Hiroyuki; Masuyama, Araki; Ryu, Ilhyong.

In: Journal of Organic Chemistry, Vol. 76, No. 17, 02.09.2011, p. 7096-7103.

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

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AU - Kobayashi, Shoji

AU - Kinoshita, Tatsuhiro

AU - Kawamoto, Takuji

AU - Wada, Masato

AU - Kuroda, Hiroyuki

AU - Masuyama, Araki

AU - Ryu, Ilhyong

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