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Synlett 1992; 1992(3): 201-203
DOI: 10.1055/s-1992-21313
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Synthetic Studies Towards Aranorosin

Alexander McKillop* , Lee McLaren, Richard J. K. Taylor, Robert J. Watson, Norman Lewis
  • *School of Chemical Sciences, University of East Anglia, Norwich NR4 7TJ, England
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Publication Date:
08 March 2002 (online)

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Hypervalent iodine reagents have been employed for the conversion of tyrosine derivatives 4a-d, 5 into 3-substituted 1-oxaspiro[4.5]deca-6,9-diene-2,8-diones 3a-d, 6, which are precursors for aranorosin synthesis. Model studies have been carried out to investigate cyclohexadienone epoxidation: dimethyldioxirane has been found to produce mono- 7, 8 and diepoxides 9,10 in good overall yield.