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Synlett 1992; 1992(5): 402-404
DOI: 10.1055/s-1992-21359
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Total Synthesis of the Lignan Antibiotic Burseran and a Novel Approach to the Podophyllotoxin Skeleton

Stephen Hanessian* , Roger Léger
  • *Department of Chemistry, Université de Montréal, C.P. 6128, Succ. A, Montréal, Québec H3C 3J7, Canada
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Publication Date:
08 March 2002 (online)

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Addition of a trimethyltin radical to allyl cinnamyl ethers 5 and 14 via a free radical process leads to the corresponding 4-substituted 3-trimethylstannylmethyltetrahydrofurans 6 and 15. Oxidative cleavage of the carbon-tin bond with ceric ammonium nitrate and subsequent transformations lead to the title compounds with a high degree of stereocontrol.

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