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Total synthesis of (-)-raumacline.
Bailey, Patrick D; Clingan, Paul D; Mills, Timothy J; Price, Richard A; Pritchard, Robin G.
Chem Commun (Camb) ; (22): 2800-1, 2003 Nov 21.
Article in English | MEDLINE | ID: mdl-14651111

ABSTRACT

The total synthesis of (-)-raumacline from L-tryptophan was achieved, featuring a cis-specific Pictet-Spengler reaction, a stereoselective Dieckmann cyclization, and an epimerization step that allowed complete stereocontrol of five chiral centres.


Subject(s)
Ajmaline/analogs & derivatives , Ajmaline/chemical synthesis , Alkaloids/chemical synthesis , Alkaloids/chemistry , Crystallography, X-Ray , Cyclization , Isomerism , Molecular Conformation , Molecular Structure , Tryptophan/chemistry
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