Total synthesis of enantiopure phalarine via a stereospecific pictet-spengler reaction: Traceless transfer of chirality from L -tryptophan Journal Article

   

Authors:	Trzupek, J. D.; Lee, D.; Crowley, B. M.; Marathias, V. M.; Danishefsky, S. J.
Article Title:	Total synthesis of enantiopure phalarine via a stereospecific pictet-spengler reaction: Traceless transfer of chirality from L -tryptophan
Abstract:	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. © 2010 American Chemical Society.
Keywords:	unclassified drug; amino acid substitution; substrate specificity; high performance liquid chromatography; amino acids; protein structure; cyclization; structure analysis; alkaloids; stereospecificity; total synthesis; synthesis (chemical); stereochemistry; stereoisomerism; tryptophan; amino acid analysis; chirality; diastereoselective; enantiopure; l-tryptophan; naturally occurring; pictet-spengler reactions; single-step; stereospecific; alkaloid; phalarine; tryptamine; amino acid synthesis; decarboxylation; enantiomer; enantioselectivity; pictet spengler reaction
Journal Title:	Journal of the American Chemical Society
Volume:	132
Issue:	24
ISSN:	0002-7863
Publisher:	American Chemical Society
Date Published:	2010-06-23
Start Page:	8506
End Page:	8512
Language:	English
DOI:	10.1021/ja1030968
PUBMED:	20509657
PROVIDER:	scopus
PMCID:	PMC2895623
DOI/URL:	http://www.scopus.com/inward/record.url?eid=2-s2.0-77953648519&partnerID=40&md5=b7b9e31154206061f64ac9815423a9c9
Notes:	--- - "Cited By (since 1996): 3" - "Export Date: 20 April 2011" - "CODEN: JACSA" - "Source: Scopus"

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