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Gold-Catalyzed Cyclization of Alkyne Alcohols: Regioselective Construction of Functionalized 6,6- and 6,7-Bicyclic Ethers.
Chem Pharm Bull (Tokyo). 2016; 64(7):845-55.CP

Abstract

We describe an efficient regioselective formation of six-/seven-membered cyclic ethers based on gold-catalyzed 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.

Authors+Show Affiliations

Graduate School of Pharmaceutical Sciences, The University of Tokyo.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

27373641

Citation

Kubota, Mio, et al. "Gold-Catalyzed Cyclization of Alkyne Alcohols: Regioselective Construction of Functionalized 6,6- and 6,7-Bicyclic Ethers." Chemical & Pharmaceutical Bulletin, vol. 64, no. 7, 2016, pp. 845-55.
Kubota M, Saito T, Miyamoto K, et al. Gold-Catalyzed Cyclization of Alkyne Alcohols: Regioselective Construction of Functionalized 6,6- and 6,7-Bicyclic Ethers. Chem Pharm Bull (Tokyo). 2016;64(7):845-55.
Kubota, M., Saito, T., Miyamoto, K., Hirano, K., Wang, C., & Uchiyama, M. (2016). Gold-Catalyzed Cyclization of Alkyne Alcohols: Regioselective Construction of Functionalized 6,6- and 6,7-Bicyclic Ethers. Chemical & Pharmaceutical Bulletin, 64(7), 845-55. https://doi.org/10.1248/cpb.c16-00204
Kubota M, et al. Gold-Catalyzed Cyclization of Alkyne Alcohols: Regioselective Construction of Functionalized 6,6- and 6,7-Bicyclic Ethers. Chem Pharm Bull (Tokyo). 2016;64(7):845-55. PubMed PMID: 27373641.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Gold-Catalyzed Cyclization of Alkyne Alcohols: 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 - 2016/7/5/entrez PY - 2016/7/5/pubmed PY - 2017/1/27/medline SP - 845 EP - 55 JF - Chemical & pharmaceutical bulletin JO - Chem Pharm Bull (Tokyo) VL - 64 IS - 7 N2 - We describe an efficient regioselective formation of six-/seven-membered cyclic ethers based on gold-catalyzed 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. SN - 1347-5223 UR - https://www.unboundmedicine.com/medline/citation/27373641/Gold_Catalyzed_Cyclization_of_Alkyne_Alcohols:_Regioselective_Construction_of_Functionalized_66__and_67_Bicyclic_Ethers_ DB - PRIME DP - Unbound Medicine ER -