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Synthesis 2000; 2000(6): 801-804
DOI: 10.1055/s-2000-6275
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Highly Efficient Synthesis of Bicyclo[3.3.1]nonane Skeleton

Jae-Deuk Yang* , Moon-Soo Kim, Miai Lee, Woonphil Baik, Sangho Koo
  • *Department of Chemistry, Myong Ji University, Yongin, Kyunggi-Do, 449-728, Korea; Fax +82 (3 35) 3 35 72 48; E-mail: sangkoo@wh.myongji.ac.kr
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Publication Date:
31 December 2000 (online)

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A highly efficient method has been developed for the construction of a bicyclo[3.3.1]nonane skeleton, which entails two consecutive tandem conjugate addition - intramolecular aldol reaction of ethyl acetoacetate (2 equiv) with conjugated enals. After hydrolysis of the double cyclization products, 6- and/or 7-substituted 1-hydroxybicyclo[3.3.1]nonan-3-ones have been obtained.

aldol reactions - bicyclic compounds - cyclizations - Michael additions - stereoselective synthesis