Synthesis of indolizidinone analogues of cytotoxic alkaloids: Monocyclic precursors are also active

Boto, Alicia; Miguélez, Javier; Marín, Raquel; Dı́az, Mario

doi:10.1016/j.bmcl.2012.03.109

Cited by 9 publications

(1 citation statement)

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“…Phenanthroindolizidine alkaloids, mainly isolated from Cynanchum, Pergularia, Tylophora , and some genera of the Asclepiadaceas family, have attracted great and long-lasting attention in the past decades for their profound biological activities, among which the excellent cytotoxic activity against various cancer cell lines is most intriguing . Among the more than 60 alkaloids of this class isolated until now, ( R )-tylophorine ( 1a ) and ( R )-antofine ( 1b ) are well-known representative 13a-H members (Figure ) .…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Approach to 13a-Methylphenanthroindolizidine Alkaloids

Cai

Wang

2012

J. Org. Chem.

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Section: Introductionmentioning

confidence: 99%

Enantioselective Approach to 13a-Methylphenanthroindolizidine Alkaloids

Cai

Wang

2012

J. Org. Chem.

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A General Strategy for the Catalytic, Highly Enantio‐ and Diastereoselective Synthesis of Indolizidine‐Based Alkaloids

Abels

Lindemann

Schneider

2014

Chemistry A European J

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Sixteen indolizidine-based alkaloids (IBAs) that were isolated as poison constituents of the skin of frogs were synthesized in a highly flexible and stereoselective manner. As a key step, a three-component, organocatalytic, highly enantio- and diastereoselective vinylogous Mukaiyama-Mannich reaction was employed furnishing optically highly enriched butyrolactams as central intermediates on a multigram scale. The attached six-membered ring was constructed through cyclization of the pendant enoate moiety onto the pyrrolidine ring. The absolute configuration of the bridgehead chiral center and the adjacent 8-position was established in the initial vinylogous Mannich reaction, whereas the 3- and 5-substituents were introduced through organometallic addition at a late stage of the synthesis with full stereochemical control from the substrate. With this strategy, simple as well as even more complex alkaloids were accessible in good overall yields as single stereoisomers. These syntheses also served to establish the absolute and relative configuration of those IBAs that had never been synthesized before.

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ChemInform Abstract: Synthesis of Indolizidinone Analogues of Cytotoxic Alkaloids: Monocyclic Precursors Are also Active.

et al. 2012

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Synthesis of Indolizidinone Analogues of Cytotoxic Alkaloids: Monocyclic PrecursorsAre also Active. -A two-step route is reported for the transformation of readily available hydroxyproline N-amides into indolizidinone derivatives of type (V) and (VI). The cytotoxic activity of the compounds is studied against the human neuroblastoma SHSY-5Y and human breast cancer MCF-7 cell lines. Especially the derivatives with the bulky biphenyl substituent (Vb) or (VIb) display cytotoxic activities at 30 μM for 48 h. The monocyclic precursors of type (VII) show a comparable or higher cytotoxicity than the bicyclic derivatives. -(BOTO*, A.; MIGUELEZ, J.; MARIN, R.; DIAZ, M.; Bioorg. Med. Chem. Lett. 22 (2012) 10, 3402-3407, http://dx.

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Synthesis of indolizidinone analogues of cytotoxic alkaloids: Monocyclic precursors are also active

Cited by 9 publications

References 56 publications

Enantioselective Approach to 13a-Methylphenanthroindolizidine Alkaloids

Enantioselective Approach to 13a-Methylphenanthroindolizidine Alkaloids

A General Strategy for the Catalytic, Highly Enantio‐ and Diastereoselective Synthesis of Indolizidine‐Based Alkaloids

ChemInform Abstract: Synthesis of Indolizidinone Analogues of Cytotoxic Alkaloids: Monocyclic Precursors Are also Active.

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