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Enantioselective total synthesis of (+)-dibromophakellstatin.
Poullennec KG, Romo D. Poullennec KG, et al. J Am Chem Soc. 2003 May 28;125(21):6344-5. doi: 10.1021/ja034575i. J Am Chem Soc. 2003. PMID: 12785755
The first enantioselective total synthesis of (+)-phakellstatin and (+)-dibromophakellstatin was achieved. Key steps in the synthesis were a desymmetrization of the diketopiperazine (S,S)-cyclo (Pro, Pro) via a diastereoselective acylation, an intramolecular Mitsunobu reac …
The first enantioselective total synthesis of (+)-phakellstatin and (+)-dibromophakellstatin was achieved. Key steps in the synthesis …
Total synthesis of (+)-dibromophakellin and (+)-dibromophakellstatin.
Imaoka T, Akimoto T, Iwamoto O, Nagasawa K. Imaoka T, et al. Chem Asian J. 2010 Aug 2;5(8):1810-6. doi: 10.1002/asia.201000213. Chem Asian J. 2010. PMID: 20564279
This methodology was applied to enantioselective total syntheses of (+)-dibromophakellin and (+)-dibromophakellstatin....
This methodology was applied to enantioselective total syntheses of (+)-dibromophakellin and (+)-dibromophakellstatin....
Palau'amine and related oroidin alkaloids dibromophakellin and dibromophakellstatin inhibit the human 20S proteasome.
Lansdell TA, Hewlett NM, Skoumbourdis AP, Fodor MD, Seiple IB, Su S, Baran PS, Feldman KS, Tepe JJ. Lansdell TA, et al. J Nat Prod. 2012 May 25;75(5):980-5. doi: 10.1021/np300231f. Epub 2012 May 16. J Nat Prod. 2012. PMID: 22591513 Free PMC article.
We report herein that the oroidin-derived alkaloids palau'amine (1), dibromophakellin (2), and dibromophakellstatin (3) inhibit the proteolytic activity of the human 20S proteasome as well as the (i)20S immunoproteasome catalytic core. ...
We report herein that the oroidin-derived alkaloids palau'amine (1), dibromophakellin (2), and dibromophakellstatin (3) inhibit the p …
Palladium-catalyzed direct functionalization of imidazolinone: synthesis of dibromophakellstatin.
Lu J, Tan X, Chen C. Lu J, et al. J Am Chem Soc. 2007 Jun 27;129(25):7768-9. doi: 10.1021/ja072844p. Epub 2007 Jun 1. J Am Chem Soc. 2007. PMID: 17539649 Free PMC article.
The direct C-H functionalization of imidazolinone is achieved with Pd(OAc)(2)/NaOAc in DMSO. Dibromophakellstatin can be synthesized in 5 steps with 40% overall yield using this new C-H activation method....
The direct C-H functionalization of imidazolinone is achieved with Pd(OAc)(2)/NaOAc in DMSO. Dibromophakellstatin can be synthesized …
Extending Pummerer reaction chemistry. Synthesis of (+/-)-dibromophakellstatin by oxidative cyclization of an imidazole derivative.
Feldman KS, Skoumbourdis AP. Feldman KS, et al. Org Lett. 2005 Mar 3;7(5):929-31. doi: 10.1021/ol0500113. Org Lett. 2005. PMID: 15727477
The thioimidate product formed by application of a new variant of the Pummerer reaction serves as a precursor to dibromophakellstatin. [reaction: see text]...
The thioimidate product formed by application of a new variant of the Pummerer reaction serves as a precursor to dibromophakellstatin …
Antineoplastic agents. 362. Isolation and X-ray crystal structure of dibromophakellstatin from the Indian ocean sponge Phakellia mauritiana.
Pettit GR, McNulty J, Herald DL, Doubek DL, Chapuis JC, Schmidt JM, Tackett LP, Boyd MR. Pettit GR, et al. J Nat Prod. 1997 Feb;60(2):180-3. doi: 10.1021/np9606106. J Nat Prod. 1997. PMID: 9051914
Bioassay-guided isolation procedures using human tumor cell lines led to isolation of dibromophakellstatin (4) from the Republic of Seychelles sponge Phakellia mauritiana. ...
Bioassay-guided isolation procedures using human tumor cell lines led to isolation of dibromophakellstatin (4) from the Republic of S …
Antitumor activity of the marine natural product dibromophakellstatin in vitro.
Zöllinger M, Kelter G, Fiebig HH, Lindel T. Zöllinger M, et al. Bioorg Med Chem Lett. 2007 Jan 15;17(2):346-9. doi: 10.1016/j.bmcl.2006.10.046. Epub 2006 Oct 24. Bioorg Med Chem Lett. 2007. PMID: 17095216
The pyrrole-imidazole alkaloid rac-dibromophakellstatin displayed selective antitumor activity in vitro when tested in 36 cell lines in a cell survival and proliferation assay. The ovarian cancer cell line OVXF 899L proved to be most sensitive (0.60 microM, IC50), followed …
The pyrrole-imidazole alkaloid rac-dibromophakellstatin displayed selective antitumor activity in vitro when tested in 36 cell lines …
Total synthesis of the cytostatic marine natural product dibromophakellstatin via three-component imidazolidinone anellation.
Zöllinger M, Mayer P, Lindel T. Zöllinger M, et al. J Org Chem. 2006 Dec 8;71(25):9431-9. doi: 10.1021/jo061813u. J Org Chem. 2006. PMID: 17137370
The tetracyclic pyrrole-imidazole alkaloid dibromophakellstatin from the marine sponge Phakellia mauritiana has been synthesized within seven steps from pyrrole in an 18% overall yield. ...Use of debrominated precursor dipyrrolopyrazinones leads to much higher anellation y …
The tetracyclic pyrrole-imidazole alkaloid dibromophakellstatin from the marine sponge Phakellia mauritiana has been synthesized with …
Hypervalent iodine-mediated vicinal syn diazidation: application to the total synthesis of (+/-)-dibromophakellstatin.
Chung R, Yu E, Incarvito CD, Austin DJ. Chung R, et al. Org Lett. 2004 Oct 28;6(22):3881-4. doi: 10.1021/ol0490532. Org Lett. 2004. PMID: 15496054
[reaction: see text] The total synthesis of (+/-)-dibromophakellstatin is described. The molecule is constructed from a key syn-diazide, formed by a hypervalent iodine-mediated diazidation of a dihydrodipyrrolopyrazinone ring structure....
[reaction: see text] The total synthesis of (+/-)-dibromophakellstatin is described. The molecule is constructed from a key syn-diazi …
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