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Synlett 1999; 1999(12): 1945-1947
DOI: 10.1055/s-1999-3174
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Synthesis of a trans-Fused Tricyclic Ether Using a Novel Differentially Protected Glucal

Michiel A. Leeuwenburgh* , Camiel Kulker, Herman S. Overkleeft, Gijsbert A. van der Marel, Jacques H. van Boom
  • *Leiden Institute of Chemistry, P.O. Box 9502, 2300 RA Leiden, The Netherlands; Fax + 31 71 5 27 43 07; E-mail: j_boom@chem.leidenuniv.nl
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Publication Date:
31 December 1999 (online)

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The construction of the trans-fused 7,6,6-ABC fragment (3) of ciguatoxin 3C, starting from the novel carbohydrate derivative 3-O-benzyl-4-O-tert-butyldimethylsilyl-6-O-trityl-d-glucal, is reported. The formation of the A- and C-rings can be effected by executing two individual ring-closing metathesis steps in a sequential or a one-pot procedure.

ring-closing metathesis - fused ethers - ciguatoxin 3C - carbohydrate - glucal