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Synthesis 2000; 2000(4): 537-540
DOI: 10.1055/s-2000-6370
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Short Enantioselective Syntheses of Both 2,7-Dimethyl-1,6-dioxaspiro[4.6]undecane and 2,7-Diethyl-1,6-dioxaspiro[4.6]undecane Using Functionalized Nitroalkane Synthons

Ghanashyam Bez* , Maitreyee Sarma Bezbarua, Anil K. Saikia, Nabin C. Barua
  • *Regional Research Laboratory, Jorhat-785006, Assam, India; Fax +91 (3 76) 32 11 58; E-mail: ncbarua@csir.res.in
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Publication Date:
31 December 2000 (online)

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ω-Nitro ketoaliphatic compounds 3a and 3b, prepared by a new and efficient route, have been elaborated to short syntheses of both 2,7-dimethyl-1,6-dioxaspiro[4.6]undecane, [(2S,5R,7S)-1a] and 2,7-diethyl-1,6-dioxaspiro[4.6]undecane [(2S,5R,7S)-1b], the pheromones produced by Andrena haemorrhoa and Andrena wilkella, respectively.

ω-nitroaliphatics - baker's yeast reduction - nonsymmetrical diketones - spiroketals - pheromones - cyclizations