Syntheses and Cytotoxicity of (R)- and (S)-7-Methoxycryptopleurine
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Title: | Syntheses and Cytotoxicity of (R)- and (S)-7-Methoxycryptopleurine |
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Authors: | Anton-Torrecillas, Cintia | Bosque, Irene | Gonzalez-Gomez, Jose C. | Loza, María Isabel | Brea, José |
Research Group/s: | Catálisis Estereoselectiva en Síntesis Orgánica (CESO) | Síntesis Asimétrica (SINTAS) |
Center, Department or Service: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Keywords: | Stereoselective | Cytotoxic | Synthesis | Phenanthroquinolizidines |
Knowledge Area: | Química Orgánica |
Issue Date: | 7-Jan-2015 |
Publisher: | American Chemical Society |
Citation: | Journal of Organic Chemistry. 2015, 80(2): 1284-1290. doi:10.1021/jo502660r |
Abstract: | Two efficient protocols are described for the transformation of a key chiral homoallyllic sulfinamine intermediate in four steps into enantioenriched 7-methoxycryptopleurine. While one of the protocols relied on a rhodium catalyzed linear hydroformylation process, the alternative approach was based on a ring-closing metathesis from the corresponding N-allyl-sulfinamine. The cytotoxic evaluation of both enantiomers of the target compound demonstrated that the (R)-compound is much more potent than its antipode against the four cancer cell lines examined. |
Sponsor: | We thank the Spanish Ministerio de Ciencia e Innovación (CTQ2011-24165) for financial support. I.B. acknowledges the Generalitat Valenciana for a postdoctoral fellowship (ACIF/2011/159). C.A.-T. thanks the ISO for a grant. |
URI: | http://hdl.handle.net/10045/44132 |
ISSN: | 0022-3263 (Print) | 1520-6904 (Online) |
DOI: | 10.1021/jo502660r |
Language: | eng |
Type: | info:eu-repo/semantics/article |
Rights: | Copyright © 2015 American Chemical Society |
Peer Review: | si |
Publisher version: | http://dx.doi.org/10.1021/jo502660r |
Appears in Collections: | INV - CESO - Artículos de Revistas INV - SINTAS - Artículos de Revistas |
Files in This Item:
File | Description | Size | Format | |
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JOC-methoxycryptopleurine.pdf | Versión final (acceso restringido) | 712,16 kB | Adobe PDF | Open Request a copy |
JOC-methoxycryptopleurine-rev.pdf | Versión revisada (acceso abierto) | 224,63 kB | Adobe PDF | Open Preview |
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