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Facile synthesis of the trans-fused azabicyclo[3.3.0]octane core of the palau'amines and the tricyclic core of the axinellamines from a common intermediate.
Org Lett. 2008 Sep 4;10(17):3685-8
PMID: 18693745
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New Tricks in Amino Acid Synthesis: Applications to Complex Natural Products.
ACS Symp Ser Am Chem Soc. 2009 Jun 14;1009:420-442
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Exploring symmetry-based logic for a synthesis of palau'amine.
J Org Chem. 2009 Aug 21;74(16):5909-19
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Spirocycloisomerization of tethered alkylidene glycocyamidines: synthesis of a base template common to the palau'amine family of alkaloids.
Angew Chem Int Ed Engl. 2005 Jan 21;44(5):765-9
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Recent advances in the Baylis-Hillman reaction and applications.
Chem Rev. 2003 Mar;103(3):811-92
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Synthetic access to the chlorocyclopentane cores of the proposed original and revised structures of palau'amine.
Angew Chem Int Ed Engl. 2008;47(36):6821-4
PMID: 18655078
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Synthesis of 1,9-dideoxy-pre-axinellamine.
Angew Chem Int Ed Engl. 2008;47(19):3578-80
PMID: 18357598
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Stable 5-substituted cyclopentadienes for the Diels-Alder cycloaddition and their application to the synthesis of palau'amine.
Angew Chem Int Ed Engl. 2008;47(46):8885-8
PMID: 18855951
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A concise asymmetric synthesis of the ADE fragment of nakadomarin A.
Org Lett. 2004 Nov 25;6(24):4539-41
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Intramolecular Diels-Alder reactions of 4-vinylimidazoles.
Org Lett. 2003 Oct 2;5(20):3623-6
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Axinellamines A-D, Novel Imidazo-Azolo-Imidazole Alkaloids from the Australian Marine Sponge Axinella sp.
J Org Chem. 1999 Feb 5;64(3):731-735
PMID: 11674140
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Natural products, stylissadines A and B, specific antagonists of the P2X7 receptor, an important inflammatory target.
J Org Chem. 2007 Mar 30;72(7):2309-17
PMID: 17315930
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Structural assignment of tetrabromostyloguanidine: does the relative configuration of the palau'amines need revision?
Angew Chem Int Ed Engl. 2007;46(13):2320-4
PMID: 17318930
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Oxidative rearrangement of imidazoles with dimethyldioxirane.
Org Lett. 2004 Mar 4;6(5):735-8
PMID: 14986962
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Highly diastereoselective desymmetrizations of cyclo(Pro,Pro): an enantioselective strategy toward phakellstatin and phakellin.
Org Lett. 2002 Aug 8;4(16):2645-8
PMID: 12153199
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Extending Pummerer reaction chemistry: application to the assembly of the pentacyclic core of dibromopalau'amine.
Org Lett. 2010 Oct 15;12(20):4532-5
PMID: 20839833
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Stereocontrolled synthesis of triazacyclopenta[cd]pentalenes by intramolecular 1,3-dipolar cycloaddition reactions of azomethine imines.
J Org Chem. 2002 Nov 1;67(22):7880-3
PMID: 12398520
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Density functional theory guided design of exo-selective dehydroalanine dienophiles for application toward the synthesis of palau'amine.
J Org Chem. 2008 Jan 4;73(1):102-10
PMID: 18067312
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Regiocontrol in Mn(III)-mediated oxidative heterobicyclizations: access to the core skeletons of oroidin dimers.
Angew Chem Int Ed Engl. 2006 Jun 26;45(26):4345-8
PMID: 16739146
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Enantioselective strategy to the spirocyclic core of Palau'amine and related bisguanidine marine alkaloids.
Org Lett. 2001 May 17;3(10):1535-8
PMID: 11388860
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Direct access to marine pyrrole-2-aminoimidazoles, oroidin, and derivatives, via new acyl-1,2-dihydropyridin intermediates.
Org Lett. 2006 Jul 6;8(14):2961-4
PMID: 16805527
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Concise, asymmetric total synthesis of spirotryprostatin A.
Org Lett. 2003 Aug 21;5(17):3135-7
PMID: 12917000
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Enantioselective total synthesis of (+)-dibromophakellstatin.
J Am Chem Soc. 2003 May 28;125(21):6344-5
PMID: 12785755
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Studies toward the total synthesis of axinellamine and massadine.
Org Lett. 2007 Sep 27;9(20):3861-4
PMID: 17803309
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Iodine(V) reagents in organic synthesis. Part 4. o-Iodoxybenzoic acid as a chemospecific tool for single electron transfer-based oxidation processes.
J Am Chem Soc. 2002 Mar 13;124(10):2245-58
PMID: 11878978
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Enantioselective synthesis of (+)-monobromophakellin and (+)-phakellin: a concise phakellin annulation strategy applicable to Palau'amine.
Angew Chem Int Ed Engl. 2008;47(7):1284-6
PMID: 18175299
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Studies toward the total synthesis of the oroidin dimers.
Org Biomol Chem. 2009 Aug 21;7(16):3215-8
PMID: 19641776
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Total syntheses of (+/-)-massadine and massadine chloride.
J Am Chem Soc. 2008 Dec 10;130(49):16490-1
PMID: 19049446
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Highly regioselective Diels-Alder reactions toward oroidin alkaloids: use of a tosylvinyl moiety as a nitrogen masking group with adjustable electronics.
Org Lett. 2005 Apr 28;7(9):1679-82
PMID: 15844879
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Total synthesis of palau'amine.
Angew Chem Int Ed Engl. 2010 Feb 1;49(6):1095-8
PMID: 20041464
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Stereocontrolled synthesis of functionalized cis-cyclopentapyrazolidines by 1,3-dipolar cycloaddition reactions of azomethine imines.
J Org Chem. 2006 Nov 24;71(24):9144-52
PMID: 17109540
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EVALUATION OF STRATEGIES FOR THE SYNTHESIS OF THE GUANIDINE HEMIAMINAL PORTION OF PALAU'AMINE.
Heterocycles. 2006 Dec 31;70:557-570
PMID: 19079749
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On the structure of palau'amine: evidence for the revised relative configuration from chemical synthesis.
J Am Chem Soc. 2007 Oct 24;129(42):12896-900
PMID: 17902668
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Synthesis and Diels-Alder reactions of 4-vinylimidazoles.
Org Lett. 2001 May 3;3(9):1319-22
PMID: 11348224
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Total synthesis of (+/-)-axinellamines A and B.
Angew Chem Int Ed Engl. 2008;47(19):3581-3
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Toward palau'amine: Hg(OTf)2-catalyzed synthesis of the cyclopentane core.
Chemistry. 2009 Jul 6;15(27):6560-3
PMID: 19492366
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A transient N-O-linked Pauson-Khand strategy for the synthesis of the deschloro carbocyclic core of the palau'amines and styloguanidines.
Org Lett. 2003 Jun 26;5(13):2203-6
PMID: 12816409