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Synlett 2000; 2000(8): 1193-1195
DOI: 10.1055/s-2000-6762
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Stereoselective Transannular Radical Cyclization of Unsaturated Cyclic Iodoacetals Yielding Medium-sized Carbocycles

Hajime Nagano* , Asako Tada, Yuko Isobe, Tomoko Yajima
  • *Department of Chemistry, Faculty of Science, Ochanomizu University, Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan; Fax + 81-3-59 78-58 98; E-mail: nagano@cc.ocha.ac.jp
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Publication Date:
31 December 2000 (online)

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Iodoacetalization of (Z)-allylic alcohols 1a - 1c in high dilution followed by transannular radical cyclization gave cis-fused bicyclic acetals 5a - 5c and 6a - 6c with high diastereoselectivities (84-93% de) and in 54-62% yields. The reaction of 2a gave 5a and 6a with 77% de, but in low yield. However, the sequential reaction of the higher homologue 1d and (E)-allylic alcohols 2b - 2d showed poor diastereoselectivities.

radical reactions - transannular cyclizations - iodo acetals - medium-sized rings - diastereoselectivity