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Synlett 1992; 1992(5): 402-404
DOI: 10.1055/s-1992-21359
DOI: 10.1055/s-1992-21359
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© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.
Total Synthesis of the Lignan Antibiotic Burseran and a Novel Approach to the Podophyllotoxin Skeleton
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Publikationsverlauf
Publikationsdatum:
08. März 2002 (online)

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.