Total synthesis of enantiopure phalarine via a stereospecific Pictet-Spengler reaction: traceless transfer of chirality from L-tryptophan.
An appropriately constructed 2-substituted derivative of l-tryptophan undergoes conversion to a prephalarine structure in a single step. The reaction occurs in a diastereoselective fashion, leading shortly thereafter to the naturally occurring version of the alkaloid phalarine.
Trzupek
John D
JD
Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10065, USA.
Lee
Dongjoo
D
Crowley
Brendan M
BM
Marathias
Vasilios M
VM
Danishefsky
Samuel J
SJ
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D014364:Tryptophan / Q000737:chemistry*
D000470:Alkaloids; C552076:phalarine; D014364:Tryptophan