Synthesis of the ABC and IJ ring fragments of yessotoxin

Tohru Oishi; Miho Suzuki; Koji Watanabe; Michio Murata

doi:10.1016/j.tetlet.2006.04.018

Synthesis of the ABC and IJ ring fragments of yessotoxin

Tohru Oishi, Miho Suzuki, Koji Watanabe, Michio Murata

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

32 Citations (Scopus)

Abstract

Synthesis of a 6/6/6 tricyclic ether system (3) corresponding to the ABC ring fragment of yessotoxin (1) has been achieved via coupling of a triflate and a 2-lithiofuran followed by intramolecular hetero-Michael addition. The IJ ring fragment (4) of 1 was readily synthesized via successive Sharpless epoxidation and 6-endo cyclization of the resulting vinyl epoxide.

Original language	English
Pages (from-to)	3975-3978
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	24
DOIs	https://doi.org/10.1016/j.tetlet.2006.04.018
Publication status	Published - Jun 12 2006
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.04.018

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title = "Synthesis of the ABC and IJ ring fragments of yessotoxin",

abstract = "Synthesis of a 6/6/6 tricyclic ether system (3) corresponding to the ABC ring fragment of yessotoxin (1) has been achieved via coupling of a triflate and a 2-lithiofuran followed by intramolecular hetero-Michael addition. The IJ ring fragment (4) of 1 was readily synthesized via successive Sharpless epoxidation and 6-endo cyclization of the resulting vinyl epoxide.",

author = "Tohru Oishi and Miho Suzuki and Koji Watanabe and Michio Murata",

note = "Funding Information: This work was supported by Grant-in-Aid for Scientific Research (B) 15350024 from JSPS and Grant-in-Aid for Scientific Research on Priority Areas 16073211 from MEXT. K.W. is grateful to the 21st Century COE Program for financial support. ",

year = "2006",

month = jun,

day = "12",

doi = "10.1016/j.tetlet.2006.04.018",

language = "English",

volume = "47",

pages = "3975--3978",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Synthesis of the ABC and IJ ring fragments of yessotoxin

AU - Oishi, Tohru

AU - Suzuki, Miho

AU - Watanabe, Koji

AU - Murata, Michio

N1 - Funding Information: This work was supported by Grant-in-Aid for Scientific Research (B) 15350024 from JSPS and Grant-in-Aid for Scientific Research on Priority Areas 16073211 from MEXT. K.W. is grateful to the 21st Century COE Program for financial support.

PY - 2006/6/12

Y1 - 2006/6/12

N2 - Synthesis of a 6/6/6 tricyclic ether system (3) corresponding to the ABC ring fragment of yessotoxin (1) has been achieved via coupling of a triflate and a 2-lithiofuran followed by intramolecular hetero-Michael addition. The IJ ring fragment (4) of 1 was readily synthesized via successive Sharpless epoxidation and 6-endo cyclization of the resulting vinyl epoxide.

AB - Synthesis of a 6/6/6 tricyclic ether system (3) corresponding to the ABC ring fragment of yessotoxin (1) has been achieved via coupling of a triflate and a 2-lithiofuran followed by intramolecular hetero-Michael addition. The IJ ring fragment (4) of 1 was readily synthesized via successive Sharpless epoxidation and 6-endo cyclization of the resulting vinyl epoxide.

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U2 - 10.1016/j.tetlet.2006.04.018

DO - 10.1016/j.tetlet.2006.04.018

M3 - Article

AN - SCOPUS:33646338173

SN - 0040-4039

VL - 47

SP - 3975

EP - 3978

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 24

ER -

Synthesis of the ABC and IJ ring fragments of yessotoxin

Abstract

All Science Journal Classification (ASJC) codes

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