Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 9, Pages 3982-3991Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo500446f
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Funding
- Spanish Ministerio de Ciencia e Innovacion [CTQ2011-24165]
- Generalitat Valenciana [ACIF/2011/159]
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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 cytotcodc activity of (+)-T7 against breast carcinoma cell line MCF-7.
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