A new synthesis of key intermediates for the assembly of polycyclic ethers: Yb(OTf)3-promoted formation of O,S-acetals from α- fluorosulfides and alcohols

Masayuki Inoue; Shuji Yamashita; Masahiro Hirama

doi:10.1016/j.tetlet.2004.01.077

A new synthesis of key intermediates for the assembly of polycyclic ethers: Yb(OTf)₃-promoted formation of O,S-acetals from α- fluorosulfides and alcohols

Masayuki Inoue, Shuji Yamashita, Masahiro Hirama

SCI - Chemistry

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

16 Citations (Scopus)

Abstract

We report a new reaction for the direct construction of O,S-acetals, key intermediates in the assembly of fused polycyclic ethers. α- Fluorosulfides and secondary alcohols were coupled by the action of Yb(OTf) ₃ to generate O,S-acetals in high yield. The neutral and selective nature of the reaction should be useful for synthesizing natural and artificial polyethers with multisensitive functionalities.

Original language	English
Pages (from-to)	2053-2056
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	10
DOIs	https://doi.org/10.1016/j.tetlet.2004.01.077
Publication status	Published - 2004 Mar 1

Keywords

Ciguatoxin
Convergent synthesis
Nucleophilic addition
O,S-Acetal
Polyether
α-Fluorosulfide

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2004.01.077

Cite this

@article{c11ab0672f95471ca098bcaaa4b23f2e,

title = "A new synthesis of key intermediates for the assembly of polycyclic ethers: Yb(OTf)3-promoted formation of O,S-acetals from α- fluorosulfides and alcohols",

abstract = "We report a new reaction for the direct construction of O,S-acetals, key intermediates in the assembly of fused polycyclic ethers. α- Fluorosulfides and secondary alcohols were coupled by the action of Yb(OTf) 3 to generate O,S-acetals in high yield. The neutral and selective nature of the reaction should be useful for synthesizing natural and artificial polyethers with multisensitive functionalities.",

keywords = "Ciguatoxin, Convergent synthesis, Nucleophilic addition, O,S-Acetal, Polyether, α-Fluorosulfide",

author = "Masayuki Inoue and Shuji Yamashita and Masahiro Hirama",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (S) from the Japan Society for the Promotion of Science (JSPS).",

year = "2004",

month = mar,

day = "1",

doi = "10.1016/j.tetlet.2004.01.077",

language = "English",

volume = "45",

pages = "2053--2056",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "10",

}

TY - JOUR

T1 - A new synthesis of key intermediates for the assembly of polycyclic ethers

T2 - Yb(OTf)3-promoted formation of O,S-acetals from α- fluorosulfides and alcohols

AU - Inoue, Masayuki

AU - Yamashita, Shuji

AU - Hirama, Masahiro

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (S) from the Japan Society for the Promotion of Science (JSPS).

PY - 2004/3/1

Y1 - 2004/3/1

N2 - We report a new reaction for the direct construction of O,S-acetals, key intermediates in the assembly of fused polycyclic ethers. α- Fluorosulfides and secondary alcohols were coupled by the action of Yb(OTf) 3 to generate O,S-acetals in high yield. The neutral and selective nature of the reaction should be useful for synthesizing natural and artificial polyethers with multisensitive functionalities.

AB - We report a new reaction for the direct construction of O,S-acetals, key intermediates in the assembly of fused polycyclic ethers. α- Fluorosulfides and secondary alcohols were coupled by the action of Yb(OTf) 3 to generate O,S-acetals in high yield. The neutral and selective nature of the reaction should be useful for synthesizing natural and artificial polyethers with multisensitive functionalities.

KW - Ciguatoxin

KW - Convergent synthesis

KW - Nucleophilic addition

KW - O,S-Acetal

KW - Polyether

KW - α-Fluorosulfide

UR - http://www.scopus.com/inward/record.url?scp=1242318517&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=1242318517&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2004.01.077

DO - 10.1016/j.tetlet.2004.01.077

M3 - Article

AN - SCOPUS:1242318517

VL - 45

SP - 2053

EP - 2056

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 10

ER -