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PMID: 21286237 Published · ppublish English Journal Article

Synthetic Studies on Palau'amine. Construction of the Cyclopentane Core via an Asymmetric 1,3-Dipolar Cycloaddition.

Tetrahedron letters ·Vol. 51 ·No. 50 ·2010-12-15 ·Pages 6557-6559

Namba K, Inai M, Sundermeier U, Greshock TJ, Williams RM

Abstract

The cyclopentane core of palau'amine has been constructed in optically pure form through the use of an asymmetric azomethine ylid [1,3]-dipolar cycloaddition reaction.

Authors & Affiliations
5 authors, click to expand affiliations / ORCID
Namba Kosuke
Department of Chemistry, Colorado State University, 1301 Center Avenue, Fort Collins, CO 80523, USA.
Inai Makto
Sundermeier Uta
Greshock Thomas J
Williams Robert M
References (37)
37 references, click to expand
  1. 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
  2. New Tricks in Amino Acid Synthesis: Applications to Complex Natural Products.
    ACS Symp Ser Am Chem Soc. 2009 Jun 14;1009:420-442 PMID: 20563264
  3. Exploring symmetry-based logic for a synthesis of palau'amine.
    J Org Chem. 2009 Aug 21;74(16):5909-19 PMID: 19603820
  4. 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 PMID: 15624220
  5. Recent advances in the Baylis-Hillman reaction and applications.
    Chem Rev. 2003 Mar;103(3):811-92 PMID: 12630854
  6. 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
  7. Synthesis of 1,9-dideoxy-pre-axinellamine.
    Angew Chem Int Ed Engl. 2008;47(19):3578-80 PMID: 18357598
  8. 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
  9. A concise asymmetric synthesis of the ADE fragment of nakadomarin A.
    Org Lett. 2004 Nov 25;6(24):4539-41 PMID: 15548070
  10. Intramolecular Diels-Alder reactions of 4-vinylimidazoles.
    Org Lett. 2003 Oct 2;5(20):3623-6 PMID: 14507188
  11. 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
  12. 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
  13. 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
  14. Oxidative rearrangement of imidazoles with dimethyldioxirane.
    Org Lett. 2004 Mar 4;6(5):735-8 PMID: 14986962
  15. 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
  16. 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
  17. 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
  18. 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
  19. 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
  20. 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
  21. 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
  22. Concise, asymmetric total synthesis of spirotryprostatin A.
    Org Lett. 2003 Aug 21;5(17):3135-7 PMID: 12917000
  23. Enantioselective total synthesis of (+)-dibromophakellstatin.
    J Am Chem Soc. 2003 May 28;125(21):6344-5 PMID: 12785755
  24. Studies toward the total synthesis of axinellamine and massadine.
    Org Lett. 2007 Sep 27;9(20):3861-4 PMID: 17803309
  25. 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
  26. 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
  27. Studies toward the total synthesis of the oroidin dimers.
    Org Biomol Chem. 2009 Aug 21;7(16):3215-8 PMID: 19641776
  28. Total syntheses of (+/-)-massadine and massadine chloride.
    J Am Chem Soc. 2008 Dec 10;130(49):16490-1 PMID: 19049446
  29. 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
  30. Total synthesis of palau'amine.
    Angew Chem Int Ed Engl. 2010 Feb 1;49(6):1095-8 PMID: 20041464
  31. 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
  32. EVALUATION OF STRATEGIES FOR THE SYNTHESIS OF THE GUANIDINE HEMIAMINAL PORTION OF PALAU'AMINE.
    Heterocycles. 2006 Dec 31;70:557-570 PMID: 19079749
  33. 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
  34. Synthesis and Diels-Alder reactions of 4-vinylimidazoles.
    Org Lett. 2001 May 3;3(9):1319-22 PMID: 11348224
  35. Total synthesis of (+/-)-axinellamines A and B.
    Angew Chem Int Ed Engl. 2008;47(19):3581-3 PMID: 18357612
  36. Toward palau'amine: Hg(OTf)2-catalyzed synthesis of the cyclopentane core.
    Chemistry. 2009 Jul 6;15(27):6560-3 PMID: 19492366
  37. 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
Article Info
Journal
Tetrahedron letters
Abbr.
Tetrahedron Lett
ISSN
0040-4039
Published
2010-12-15
Pages
6557-6559
Language
English
Region
England
NLM ID
2984819R
PMCID
PMC3030269
Grants
NIGMS NIH HHS · R01 GM068011-06 · United States
NIGMS NIH HHS · R01 GM068011-05A1 · United States
NIGMS NIH HHS · R01 GM068011-08 · United States
NIGMS NIH HHS · R01 GM068011 · United States
NIGMS NIH HHS · R01 GM068011-07 · United States
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