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Ring Closure Reactions of Disubstituted 4-Penten-1-oxyl Radicals − Towards a Stereoselective Synthesis of allo-Muscarine

✍ Scribed by Jens Hartung; Rainer Kneuer

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 326 KB
Volume: 2000
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(200005)2000:9<1677::aid-ejoc1677>3.0.co;2-x

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✦ Synopsis

The trisubstituted functionalized tetrahydrofurans 10, 11, 16, 18, and 19 were photochemically prepared from 2,3-syn-and 2,3-anti-configured N-(3-benzoyloxy-5-hexen-2-oxy)thiazole-2(3H)-thione anti-6, pyridinethiones 7, anti-8, and BrCCl 3 . The formation of tetrahydrofurans was achieved by an efficient and highly regioselective alkoxyl radical cyclization (5-exo-trig). The 2,3-anti substituted intermediates 9 and 12 cyclize stereoselectively whereas a 2,3-syn-configured O-

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