Literature DB >> 19603820

Exploring symmetry-based logic for a synthesis of palau'amine.

Qingyi Li1, Paul Hurley, Hui Ding, Andrew G Roberts, Radha Akella, Patrick G Harran.   

Abstract

A synthetic approach to palau'amine is described that exploits veiled symmetry in the structure. Bis-alkylidenes i have been prepared and found susceptible to halogenative desymmetrization using t-BuOCl. This oxidation forms the imbedded spirocyclopentane motif observed in the natural product. A host of atypical reactions and processes developed during these studies are discussed, as are plans for completing total syntheses of this compound class.

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Year:  2009        PMID： 19603820      PMCID： PMC2888864          DOI： 10.1021/jo900755r

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  23 in total

1.  Spirocycloisomerization of tethered alkylidene glycocyamidines: synthesis of a base template common to the palau'amine family of alkaloids.

Authors:  Hugo Garrido-Hernandez; Masakazu Nakadai; Marc Vimolratana; Qingyi Li; Thomas Doundoulakis; Patrick G Harran
Journal:  Angew Chem Int Ed Engl       Date:  2005-01-21       Impact factor: 15.336

2.  Total synthesis of (+/-)-axinellamines A and B.

Authors:  Daniel P O'Malley; Junichiro Yamaguchi; Ian S Young; Ian B Seiple; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Sceptrin as a potential biosynthetic precursor to complex pyrrole-imidazole alkaloids: the total synthesis of ageliferin.

Authors:  Phil S Baran; Daniel P O'Malley; Alexandros L Zografos
Journal:  Angew Chem Int Ed Engl       Date:  2004-05-10       Impact factor: 15.336

4.  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.

Authors:  Manuel A Zancanella; Daniel Romo
Journal:  Org Lett       Date:  2008-08-12       Impact factor: 6.005

5.  Stable 5-substituted cyclopentadienes for the Diels-Alder cycloaddition and their application to the synthesis of palau'amine.

Authors:  Jonathan Hudon; Timothy A Cernak; James A Ashenhurst; James L Gleason
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water.

Authors:  Kevin W Anderson; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2005-09-26       Impact factor: 15.336

7.  Disubstituted imidazolium-2-carboxylates as efficient precursors to N-heterocyclic carbene complexes of Rh, Ru, Ir, and Pd.

Authors:  Adelina M Voutchkova; Leah N Appelhans; Anthony R Chianese; Robert H Crabtree
Journal:  J Am Chem Soc       Date:  2005-12-21       Impact factor: 15.419

8.  Verpacamides A-D, a sequence of C11N5 diketopiperazines relating cyclo(Pro-Pro) to cyclo(Pro-Arg), from the marine sponge Axinella vaceleti: possible biogenetic precursors of pyrrole-2-aminoimidazole alkaloids.

Authors:  Carine Vergne; Nicole Boury-Esnault; Thierry Perez; Marie-Thérèse Martin; Marie-Thérèse Adeline; Elise Tran Huu Dau; Ali Al-Mourabit
Journal:  Org Lett       Date:  2006-05-25       Impact factor: 6.005

9.  Total syntheses of (+/-)-massadine and massadine chloride.

Authors:  Shun Su; Ian B Seiple; Ian S Young; Phil S Baran
Journal:  J Am Chem Soc       Date:  2008-12-10       Impact factor: 15.419

10.  Density functional theory guided design of exo-selective dehydroalanine dienophiles for application toward the synthesis of palau'amine.

Authors:  Timothy A Cernak; James L Gleason
Journal:  J Org Chem       Date:  2007-12-08       Impact factor: 4.354
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  14 in total

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

Authors:  Kosuke Namba; Makto Inai; Uta Sundermeier; Thomas J Greshock; Robert M Williams
Journal:  Tetrahedron Lett       Date:  2010-12-15       Impact factor: 2.415

2.  Asymmetric synthesis of ageliferin.

Authors:  Xiao Wang; Zhiqiang Ma; Jianming Lu; Xianghui Tan; Chuo Chen
Journal:  J Am Chem Soc       Date:  2011-09-08       Impact factor: 15.419

3.  Pyrrole aminoimidazole alkaloid metabiosynthesis with marine sponges Agelas conifera and Stylissa caribica.

Authors:  E Paige Stout; Yong-Gang Wang; Daniel Romo; Tadeusz F Molinski
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-04       Impact factor: 15.336

4.  Synthetic (±)-axinellamines deficient in halogen.

Authors:  Hui Ding; Andrew G Roberts; Patrick G Harran
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-19       Impact factor: 15.336

5.  Enantioselective total syntheses of (-)-palau'amine, (-)-axinellamines, and (-)-massadines.

Authors:  Ian B Seiple; Shun Su; Ian S Young; Akifumi Nakamura; Junichiro Yamaguchi; Lars Jørgensen; Rodrigo A Rodriguez; Daniel P O'Malley; Tanja Gaich; Matthias Köck; Phil S Baran
Journal:  J Am Chem Soc       Date:  2011-08-23       Impact factor: 15.419

Review 6.  Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids.

Authors:  Ali Al-Mourabit; Manuel A Zancanella; Supriya Tilvi; Daniel Romo
Journal:  Nat Prod Rep       Date:  2011-05-09       Impact factor: 13.423

7.  Scalable, stereocontrolled total syntheses of (±)-axinellamines A and B.

Authors:  Shun Su; Rodrigo A Rodriguez; Phil S Baran
Journal:  J Am Chem Soc       Date:  2011-08-16       Impact factor: 15.419

8.  A biomimetic route for construction of the [4+2] and [3+2] core skeletons of dimeric pyrrole-imidazole alkaloids and asymmetric synthesis of ageliferins.

Authors:  Xiao Wang; Xiaolei Wang; Xianghui Tan; Jianming Lu; Kevin W Cormier; Zhiqiang Ma; Chuo Chen
Journal:  J Am Chem Soc       Date:  2012-11-02       Impact factor: 15.419

9.  Total Synthesis of Ageliferin via Acyl N-amidinyliminium Ion Rearrangement.

Authors:  Hui Ding; Andrew G Roberts; Patrick G Harran
Journal:  Chem Sci       Date:  2013-01-01       Impact factor: 9.825

Review 10.  A submarine journey: the pyrrole-imidazole alkaloids.

Authors:  Barbara Forte; Beatrice Malgesini; Claudia Piutti; Francesca Quartieri; Alessandra Scolaro; Gianluca Papeo
Journal:  Mar Drugs       Date:  2009-11-27       Impact factor: 5.118
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