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

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

^b Advanced Science Institute, NanomedicalEngineering Laboratory, RIKEN, 2-1 Hirasawa, Saitama 351-0198, Wako-shi, Japan

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

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

Abstract

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.

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†

Abstract

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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

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