Chemical predisposition in synthesis: application to the preparation of the pyrrolidine natural products, plakoridines A and B

The pyrrolidine natural products, plakoridines A and B, as well as an array of unnatural analogues, have been prepared using a five-step synthetic sequence modelled on a biogenetic theory. The key transformation involves a ‘Mannich/Michael/internal-redox’ cascade, which proceeds in yields of 31–63%....

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Bibliographic Details
Published in:Tetrahedron 2006-11, Vol.62 (47), p.10914-10927
Main Authors: Etchells, Laura L., Helliwell, Madeleine, Kershaw, Neil M., Sardarian, Ali, Whitehead, Roger C.
Format: Article
Language:English
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Summary:The pyrrolidine natural products, plakoridines A and B, as well as an array of unnatural analogues, have been prepared using a five-step synthetic sequence modelled on a biogenetic theory. The key transformation involves a ‘Mannich/Michael/internal-redox’ cascade, which proceeds in yields of 31–63%. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2006.08.075