Tuning efficiency of the 4-exo-trig cyclization by the electronic effect: ring closure of 3,3-difluoro-4-pentenyl carbon radicals and synthesis of a gem-difluorocyclobutane nucleoside

Hiroki Kumamoto; Sachiko Kawahigashi; Hiromi Wakabayashi; Tomohiko Nakano; Tomoko Miyaike; Yasuyuki Kitagawa; Hiroshi Abe; Mika Ito; Kazuhiro Haraguchi; Jan Balzarini; Masanori Baba; Hiromichi Tanaka

doi:10.1039/C2CC35876J

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Chemical Communications

Issue 89, 2012

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Tuning efficiency of the 4-exo-trig cyclization by the electronic effect: ring closure of 3,3-difluoro-4-pentenyl carbon radicals and synthesis of a gem-difluorocyclobutane nucleoside

Hiroki Kumamoto,*^a Sachiko Kawahigashi,^a Hiromi Wakabayashi,^a Tomohiko Nakano,^a Tomoko Miyaike,^a Yasuyuki Kitagawa,^a Hiroshi Abe,^b Mika Ito,^b Kazuhiro Haraguchi,^a Jan Balzarini,^c Masanori Baba^d and Hiromichi Tanaka^a

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School of Pharmacy, Showa University, 1-5-8 Hatanodai, Tokyo 142-8555, Japan
E-mail: kumamoto@pharm.showa-u.ac.jp ;
Fax: +81-3-3784-8252 ;
Tel: +81-3-3784-8187

Advanced Science Institute, NanomedicalEngineering Laboratory, RIKEN, 2-1 Hirasawa, Saitama 351-0198, Japan

Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000 Leuven, Belgium

Division of Antiviral Chemotherapy, Center for Chronic Viral Diseases, Graduate School of Medical and Dental Sciences, Kagoshima University, Kagoshima 89-8544, Japan

Chem. Commun., 2012,48, 10993-10995

DOI: 10.1039/C2CC35876J
Received 14 Aug 2012, Accepted 20 Sep 2012
First published online 24 Sep 2012

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4-exo-trig Cyclization reaction of a 4-pentenyl carbon radical containing the gem-difluoromethylene moiety adjacent to a radical accepting α,β-unsaturated ester was found to proceed efficiently to furnish a novel gem-difluorocyclobutane derivative. The cyclized product could be transformed into a gem-difluoromethylene analogue of oxetanocin T.

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Chemical Communications

Tuning efficiency of the 4-exo-trig cyclization by the electronic effect: ring closure of 3,3-difluoro-4-pentenyl carbon radicals and synthesis of a gem-difluorocyclobutane nucleoside

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Chemical Communications

Tuning efficiency of the 4-exo-trig cyclization by the electronic effect: ring closure of 3,3-difluoro-4-pentenyl carbon radicals and synthesis of a gem-difluorocyclobutane nucleoside

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