Gold-catalyzed cyclization of alkyne alcohols: Regioselective construction of functionalized 6,6- and 6,7-bicyclic ethers

Mio Kubota; Tatsuo Saito; Kazunori Miyamoto; Keiichi Hirano; Chao Wang; Masanobu Uchiyama

doi:10.1248/cpb.c16-00204

Gold-catalyzed cyclization of alkyne alcohols: Regioselective construction of functionalized 6,6- and 6,7-bicyclic ethers

Mio Kubota
, Tatsuo Saito
, Kazunori Miyamoto
, Keiichi Hirano
, Chao Wang
, Masanobu Uchiyama

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

12 Citations (Scopus)

Abstract

We describe an efficient regioselective formation of six-/seven-membered cyclic ethers based on goldcatalyzed intramolecular hydroalkoxylation. Sequential gold-catalyzed cyclization and palladium-catalyzed cross-coupling reactions afforded 6,6-bicyclic ethers, while reversing the reaction sequence (cross-coupling then cyclization) afforded 6,7-bicyclic ethers. This methodology should provide access to a range of functional polycyclic ethers.

Original language	English
Pages (from-to)	845-855
Number of pages	11
Journal	Chemical and Pharmaceutical Bulletin
Volume	64
Issue number	7
DOIs	https://doi.org/10.1248/cpb.c16-00204
Publication status	Published - 2016
Externally published	Yes

Keywords

Cyclization
Gold-catalysis
Hydroalkoxylation
Polyether
Tandem reaction

ASJC Scopus subject areas

General Chemistry
Drug Discovery

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10.1248/cpb.c16-00204

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title = "Gold-catalyzed cyclization of alkyne alcohols: Regioselective construction of functionalized 6,6- and 6,7-bicyclic ethers",

abstract = "We describe an efficient regioselective formation of six-/seven-membered cyclic ethers based on goldcatalyzed intramolecular hydroalkoxylation. Sequential gold-catalyzed cyclization and palladium-catalyzed cross-coupling reactions afforded 6,6-bicyclic ethers, while reversing the reaction sequence (cross-coupling then cyclization) afforded 6,7-bicyclic ethers. This methodology should provide access to a range of functional polycyclic ethers.",

keywords = "Cyclization, Gold-catalysis, Hydroalkoxylation, Polyether, Tandem reaction",

author = "Mio Kubota and Tatsuo Saito and Kazunori Miyamoto and Keiichi Hirano and Chao Wang and Masanobu Uchiyama",

note = "Publisher Copyright: {\textcopyright} 2016 The Pharmaceutical Society of Japan.",

year = "2016",

doi = "10.1248/cpb.c16-00204",

language = "English",

volume = "64",

pages = "845--855",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

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TY - JOUR

T1 - Gold-catalyzed cyclization of alkyne alcohols

T2 - Regioselective construction of functionalized 6,6- and 6,7-bicyclic ethers

AU - Kubota, Mio

AU - Saito, Tatsuo

AU - Miyamoto, Kazunori

AU - Hirano, Keiichi

AU - Wang, Chao

AU - Uchiyama, Masanobu

PY - 2016

Y1 - 2016

N2 - We describe an efficient regioselective formation of six-/seven-membered cyclic ethers based on goldcatalyzed intramolecular hydroalkoxylation. Sequential gold-catalyzed cyclization and palladium-catalyzed cross-coupling reactions afforded 6,6-bicyclic ethers, while reversing the reaction sequence (cross-coupling then cyclization) afforded 6,7-bicyclic ethers. This methodology should provide access to a range of functional polycyclic ethers.

AB - We describe an efficient regioselective formation of six-/seven-membered cyclic ethers based on goldcatalyzed intramolecular hydroalkoxylation. Sequential gold-catalyzed cyclization and palladium-catalyzed cross-coupling reactions afforded 6,6-bicyclic ethers, while reversing the reaction sequence (cross-coupling then cyclization) afforded 6,7-bicyclic ethers. This methodology should provide access to a range of functional polycyclic ethers.

KW - Cyclization

KW - Gold-catalysis

KW - Hydroalkoxylation

KW - Polyether

KW - Tandem reaction

UR - https://www.scopus.com/pages/publications/84977279712

UR - https://www.scopus.com/pages/publications/84977279712#tab=citedBy

U2 - 10.1248/cpb.c16-00204

DO - 10.1248/cpb.c16-00204

M3 - Article

C2 - 27373641

AN - SCOPUS:84977279712

SN - 0009-2363

VL - 64

SP - 845

EP - 855

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 7

ER -

Gold-catalyzed cyclization of alkyne alcohols: Regioselective construction of functionalized 6,6- and 6,7-bicyclic ethers

Abstract

Keywords

ASJC Scopus subject areas

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