Syntheses and Cytotoxicity of (R)- and (S)-7-Methoxycryptopleurine

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Title: Syntheses and Cytotoxicity of (R)- and (S)-7-Methoxycryptopleurine
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.
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
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Appears in Collections:INV - CESO - Artículos de Revistas
INV - SINTAS - Artículos de Revistas

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