Stereocontrolled synthesis of the IJK ring segment of yessotoxin

Isao Kadota; Takashi Abe; Yuki Sato; Chizuko Kabuto; Yoshinori Yamamoto

doi:10.1016/j.tetlet.2006.07.027

Stereocontrolled synthesis of the IJK ring segment of yessotoxin

Isao Kadota, Takashi Abe, Yuki Sato, Chizuko Kabuto, Yoshinori Yamamoto

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

12 Citations (Scopus)

Abstract

A stereocontrolled synthesis of the IJK ring segment of yessotoxin is described. Cyclization of 11 mediated by SmI₂ gave the IJ ring system 12 as the sole product. Construction of the K ring moiety was performed by the acid catalyzed cyclization of epoxy alcohol 20 to afford the IJK ring segment in a highly stereocontrolled manner.

Original language	English
Pages (from-to)	6545-6548
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	37
DOIs	https://doi.org/10.1016/j.tetlet.2006.07.027
Publication status	Published - Sept 11 2006
Externally published	Yes

Keywords

Cyclization
Polycyclic ethers
Yessotoxin

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.07.027

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title = "Stereocontrolled synthesis of the IJK ring segment of yessotoxin",

abstract = "A stereocontrolled synthesis of the IJK ring segment of yessotoxin is described. Cyclization of 11 mediated by SmI2 gave the IJ ring system 12 as the sole product. Construction of the K ring moiety was performed by the acid catalyzed cyclization of epoxy alcohol 20 to afford the IJK ring segment in a highly stereocontrolled manner.",

keywords = "Cyclization, Polycyclic ethers, Yessotoxin",

author = "Isao Kadota and Takashi Abe and Yuki Sato and Chizuko Kabuto and Yoshinori Yamamoto",

note = "Funding Information: This work was financially supported by the Novartis Foundation for the Promotion of Science, the Kurata Memorial Hitachi Science and Technology Foundation, the Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan. ",

year = "2006",

month = sep,

day = "11",

doi = "10.1016/j.tetlet.2006.07.027",

language = "English",

volume = "47",

pages = "6545--6548",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "37",

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TY - JOUR

T1 - Stereocontrolled synthesis of the IJK ring segment of yessotoxin

AU - Kadota, Isao

AU - Abe, Takashi

AU - Sato, Yuki

AU - Kabuto, Chizuko

AU - Yamamoto, Yoshinori

N1 - Funding Information: This work was financially supported by the Novartis Foundation for the Promotion of Science, the Kurata Memorial Hitachi Science and Technology Foundation, the Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

PY - 2006/9/11

Y1 - 2006/9/11

N2 - A stereocontrolled synthesis of the IJK ring segment of yessotoxin is described. Cyclization of 11 mediated by SmI2 gave the IJ ring system 12 as the sole product. Construction of the K ring moiety was performed by the acid catalyzed cyclization of epoxy alcohol 20 to afford the IJK ring segment in a highly stereocontrolled manner.

AB - A stereocontrolled synthesis of the IJK ring segment of yessotoxin is described. Cyclization of 11 mediated by SmI2 gave the IJ ring system 12 as the sole product. Construction of the K ring moiety was performed by the acid catalyzed cyclization of epoxy alcohol 20 to afford the IJK ring segment in a highly stereocontrolled manner.

KW - Cyclization

KW - Polycyclic ethers

KW - Yessotoxin

UR - http://www.scopus.com/inward/record.url?scp=33746819762&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33746819762&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2006.07.027

DO - 10.1016/j.tetlet.2006.07.027

M3 - Article

AN - SCOPUS:33746819762

SN - 0040-4039

VL - 47

SP - 6545

EP - 6548

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

Stereocontrolled synthesis of the IJK ring segment of yessotoxin

Abstract

Keywords

ASJC Scopus subject areas

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