A Concise Sultone Route to Highly Oxygenated 1,10-seco-Eudesmanolides – Enantioselective Total Synthesis of the Antileukemic Sesquiterpene Lactones(–)-Eriolanin and (–)-Eriolangin

Autor:	Rolan D Fröhlich, Peter Metz, André Hennig, Pia Schwab, Jörn Merten, Sergey V. Tokalov, Herwig O. Gutzeit
Rok vydání:	2006
Předmět:	Human leukemia chemistry.chemical_compound Eriolangin chemistry Stereochemistry Organic Chemistry Enantioselective synthesis Absolute configuration Total synthesis Organic chemistry Physical and Theoretical Chemistry Sesquiterpene Terpenoid
Zdroj:	European Journal of Organic Chemistry. 2006:1144-1161
ISSN:	1099-0690 1434-193X
DOI:	10.1002/ejoc.200500739
Popis:	Using a sultone as the key intermediate, the first enantioselective total synthesis of the antileukemic 1,10-seco-eudesmanolides (–)-eriolanin (1) and (–)-eriolangin (2) was achieved, which also established the hitherto unknown absolute configuration of these sesquiterpene lactones. Starting from 2-bromo-1-(2-furyl)ethanone, 24 steps were required to generate the common basic structure and two additional steps in each case for completion of the natural products. The effect of 1 and 2 on the cell cycle of human leukemia (HL-60) cells was investigated by flow cytometry. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
Databáze:	OpenAIRE
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