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

Access to Document

10.1021/jo201064h

Fingerprint Dive into the research topics of 'Stereocontrolled synthesis of substituted bicyclic ethers through oxy-Favorskii rearrangement: Total synthesis of (±)-communiol e'. Together they form a unique fingerprint.

Cite this

@article{8a33d5392c1643799d5878c46a155921,

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.",

author = "Shoji Kobayashi and Tatsuhiro Kinoshita and Takuji Kawamoto and Masato Wada and Hiroyuki Kuroda and Araki Masuyama and Ilhyong Ryu",

year = "2011",

month = sep,

day = "2",

doi = "10.1021/jo201064h",

language = "English",

volume = "76",

pages = "7096--7103",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "17",

}

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

TY - JOUR

T1 - Stereocontrolled synthesis of substituted bicyclic ethers through oxy-Favorskii rearrangement

T2 - Total synthesis of (±)-communiol e

AU - Kobayashi, Shoji

AU - Kinoshita, Tatsuhiro

AU - Kawamoto, Takuji

AU - Wada, Masato

AU - Kuroda, Hiroyuki

AU - Masuyama, Araki

AU - Ryu, Ilhyong

PY - 2011/9/2

Y1 - 2011/9/2

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=80052153437&partnerID=8YFLogxK

U2 - 10.1021/jo201064h

DO - 10.1021/jo201064h

M3 - Article

C2 - 21786776

AN - SCOPUS:80052153437

VL - 76

SP - 7096

EP - 7103

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 17

ER -

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

Abstract

Access to Document

Other files and links

Cite this