Total Synthesis of Sedum Alkaloids via Catalyst Controlled aza-Cope Rearrangement and Hydroformylation with Formaldehyde

The catalytic asymmetric aminoallylation of chiral aldehydes is developed as a new method for the catalyst controlled synthesis of syn- and anti-1,3-aminoalcohols. This methodology is highlighted in the synthesis of the sedum alkaloids (+)-sedridine and (+)-allosedridine both of which have their fin...

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Bibliographic Details
Published in:Organic letters 2013-01, Vol.15 (2), p.242-245
Main Authors: Ren, Hong, Wulff, William D
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Amino Alcohols - chemical synthesis
Amino Alcohols - chemistry
Catalysis
Formaldehyde - chemistry
Piperidines - chemical synthesis
Piperidines - chemistry
Sedum - chemistry
Stereoisomerism
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Summary:The catalytic asymmetric aminoallylation of chiral aldehydes is developed as a new method for the catalyst controlled synthesis of syn- and anti-1,3-aminoalcohols. This methodology is highlighted in the synthesis of the sedum alkaloids (+)-sedridine and (+)-allosedridine both of which have their final carbon incorporated during closure of the piperidine ring via a hydroformylation with formaldehyde.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol302769r