Natural Tetraponerines: A General Synthesis and Antiproliferative Activity

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Title: Natural Tetraponerines: A General Synthesis and Antiproliferative Activity
Authors: 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: Natural tetraponerines | Synthesis | Antiproliferative
Knowledge Area: Química Orgánica
Issue Date: 14-Apr-2014
Publisher: American Chemical Society
Citation: Journal of Organic Chemistry. 2014, 79(9): 3982-3991. doi:10.1021/jo500446f
Abstract: A stereocontrolled general methodology to access all natural tetraponerines from (+)-T1 to (+)-T8 is detailed. Two consecutive indium-mediated aminoallylations with the appropriate enantiomer of chiral N-tert-butylsulfinamide and a thermodynamic control at the aminal stereocenter allow the formation of each natural tetraponerine with excellent stereoselectivity. The use of 4-bromobutanal in the first aminoallylation leads to the formation of 5–6–5 tetraponerines, while 5-bromopentanal is required to build the scaffold of 6–6–5 tetraponerines. A cross-metathesis reaction of the second aminoallylation product with cis-3-hexene is used to elongate the side chain up to 5 carbons so as to prepare the tetraponerines T5 to T8. The anticancer activity of these heavier tetraponerines against four different carcinoma human cell lines is examined, observing a promising cytotoxic activity of (+)-T7 against breast carcinoma cell line MCF-7.
Sponsor: We thank the Spanish Ministerio de Ciencia e Innovación for their financial support (CTQ2011-24165). I.B. acknowledges the Generalitat Valenciana for a predoctoral fellowship (ACIF/2011/159).
ISSN: 0022-3263 (Print) | 1520-6904 (Online)
DOI: 10.1021/jo500446f
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2014 American Chemical Society
Peer Review: si
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Appears in Collections:INV - SINTAS - Artículos de Revistas
INV - CESO - Artículos de Revistas

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