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Revised structures of dehydrostenines A and B: total syntheses of (±)-dehydrostenine A and structure assigned to dehydrostenine B

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Olivier, WJ ORCID: 0000-0002-8838-9609, Lucas, NT, Bissember, AC ORCID: 0000-0001-5515-2878 and Smith, JA ORCID: 0000-0001-6313-3298 2021 , 'Revised structures of dehydrostenines A and B: total syntheses of (±)-dehydrostenine A and structure assigned to dehydrostenine B' , Chemistry: A European Journal, vol. 27, no. 62 , pp. 15382-15386 , doi: 10.1002/chem.202102651.

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Abstract

The first total syntheses of the Stemona alkaloiddehydrostenine A and the structure assigned to dehydrostenineB have been completed from a simple pyrrolesubstrate in 10 and 11 steps, respectively. Two independentBrønsted-acid-mediated intramolecular Michael additionswere exploited to construct the tetracyclic dehydrosteninecore. As a result of synthetic studies and associated analysisof the relevant literature, revisions of the structuresoriginally assigned to dehydrostenines A and B areproposed.

Item Type: Article
Authors/Creators:Olivier, WJ and Lucas, NT and Bissember, AC and Smith, JA
Keywords: dehydrostenines, pyrrole, Stemona alkaloids, total synthesis
Journal or Publication Title: Chemistry: A European Journal
Publisher: Wiley-V C H Verlag Gmbh
ISSN: 0947-6539
DOI / ID Number: 10.1002/chem.202102651
Copyright Information:

© 2021 Wiley-VCH GmbH

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