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

Chem Commun (Camb). 2012 Nov 18;48(89):10993-5. doi: 10.1039/c2cc35876j.

Authors

Hiroki Kumamoto¹, Sachiko Kawahigashi, Hiromi Wakabayashi, Tomohiko Nakano, Tomoko Miyaike, Yasuyuki Kitagawa, Hiroshi Abe, Mika Ito, Kazuhiro Haraguchi, Jan Balzarini, Masanori Baba, Hiromichi Tanaka

Affiliation

¹ School of Pharmacy, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan. [email protected]

PMID: 23038212
DOI: 10.1039/c2cc35876j

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Adenine / analogs & derivatives*
Adenine / chemical synthesis
Adenine / chemistry
Alkenes / chemistry
Butanes / chemical synthesis
Butanes / chemistry*
Carbon / chemistry*
Cyclization
Fluorine / chemistry*
Free Radicals
Molecular Structure
Nucleosides / chemical synthesis
Nucleosides / chemistry*

Substances

Alkenes
Butanes
Free Radicals
Nucleosides
oxetanocin
Fluorine
butane
Carbon
Adenine