Total synthesis of (-)-raumacline.
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.
Bailey
Patrick D
PD
Department of Chemistry, UMIST, PO Box 88, Manchester, UK M60 1QD. p.bailey@umist.ac.uk
Clingan
Paul D
PD
Mills
Timothy J
TJ
Price
Richard A
RA
Pritchard
Robin G
RG
D000404:Ajmaline / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D007536:Isomerism; D008968:Molecular Conformation; D015394:Molecular Structure; D014364:Tryptophan / Q000737:chemistry
D000470:Alkaloids; C493401:raumacline; D000404:Ajmaline; D014364:Tryptophan