2006
DOI: 10.1016/j.tetlet.2006.02.035
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Two-step synthesis of the bipyrrole precursor of prodigiosins

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Cited by 68 publications
(80 citation statements)
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“…Intrigued by their pharmaceutical prospects, the total synthesis of prodiginine-type compounds has been reported [19]. Moreover, a synthetic analog named GX15-070 has been used in phase I/II clinical trials for cancer treatment [20]. However, other analogs anticipated to have even more antitumor activity, such as streptorubin B (butylmeta-cycloheptylprodiginine, Scheme 1), were difficult to synthesize in the lab.…”
mentioning
confidence: 99%
“…Intrigued by their pharmaceutical prospects, the total synthesis of prodiginine-type compounds has been reported [19]. Moreover, a synthetic analog named GX15-070 has been used in phase I/II clinical trials for cancer treatment [20]. However, other analogs anticipated to have even more antitumor activity, such as streptorubin B (butylmeta-cycloheptylprodiginine, Scheme 1), were difficult to synthesize in the lab.…”
mentioning
confidence: 99%
“…202 Another member of this family of natural products has been obtained by palladium-catalyzed coupling of the boron derivative 100 with a pyrrolyl triflate. 203 This pyrrole boronic acid compound has also been employed in other cross-coupling reactions, 204 including progesterone receptor modulators 205 and the total synthesis of ageladine A.…”
Section: Aromatic Five-membered Ringsmentioning
confidence: 99%
“…5 An alternative strategy to generate the bipyrrolic unit was recently developed by Dairi et al (path B, Scheme 1) and involves the synthesis of a 2-formyl bipyrrole in a two-step route from 4-methoxy-3-pyrrolin-2-one. 8,9 Unfortunately, this process was not successful in our hands as the 2-formyl bipyrrole could only be isolated in low and irreproducible yields.Path C is relatively more convenient and has traditionally relied on a base-promoted condensation of a 2-formyl pyrrole with a pyrrolin-2-one to generate the dipyrrinone unit, followed by formation of the triflated analogues and then Suzuki coupling to the final pyrrolyl-dipyrrin skeletons. 3 However, the base-promoted condensation step of this process to generate the dipyrrinones suffers serious limitations due to the equilibrium between the retro 2-formyl pyrrole in the presence of strong base, as observed by others during the synthesis of metacycloprodigiosin.…”
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confidence: 94%