Literature DB >> 21286237

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

Kosuke Namba1, Makto Inai, Uta Sundermeier, Thomas J Greshock, Robert M Williams.   

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.

Entities:  

Year:  2010        PMID： 21286237      PMCID： PMC3030269          DOI： 10.1016/j.tetlet.2010.10.037

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  37 in total

1.  Extending Pummerer reaction chemistry: application to the assembly of the pentacyclic core of dibromopalau'amine.

Authors:  Ken S Feldman; Ahmed Yimam Nuriye
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

2.  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

3.  EVALUATION OF STRATEGIES FOR THE SYNTHESIS OF THE GUANIDINE HEMIAMINAL PORTION OF PALAU'AMINE.

Authors:  Brian A Lanman; Larry E Overman
Journal:  Heterocycles       Date:  2006-12-31       Impact factor: 0.831

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.  Regiocontrol in Mn(III)-mediated oxidative heterobicyclizations: access to the core skeletons of oroidin dimers.

Authors:  Xianghui Tan; Chuo Chen
Journal:  Angew Chem Int Ed Engl       Date:  2006-06-26       Impact factor: 15.336

7.  Enantioselective total synthesis of (+)-dibromophakellstatin.

Authors:  Karine G Poullennec; Daniel Romo
Journal:  J Am Chem Soc       Date:  2003-05-28       Impact factor: 15.419

8.  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

9.  A concise asymmetric synthesis of the ADE fragment of nakadomarin A.

Authors:  Kateri A Ahrendt; Robert M Williams
Journal:  Org Lett       Date:  2004-11-25       Impact factor: 6.005

10.  Oxidative rearrangement of imidazoles with dimethyldioxirane.

Authors:  Carl J Lovely; Hongwang Du; Yong He; H V Rasika Dias
Journal:  Org Lett       Date:  2004-03-04       Impact factor: 6.005
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  13 in total

Review 1.  Natural products synthesis: enabling tools to penetrate Nature's secrets of biogenesis and biomechanism.

Authors:  Robert M Williams
Journal:  J Org Chem       Date:  2011-04-12       Impact factor: 4.354

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.  Syntheses of Cyclic Guanidine-Containing Natural Products.

Authors:  Yuyong Ma; Saptarshi De; Chuo Chen
Journal:  Tetrahedron       Date:  2015-02-25       Impact factor: 2.457

4.  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 5.  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

6.  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

7.  Enantioselective synthesis of angularly substituted 1-azabicylic rings: coupled dynamic kinetic epimerization and chirality transfer.

Authors:  Zachary D Aron; Tatsuya Ito; Tricia L May; Larry E Overman; Jocelyn Wang
Journal:  J Org Chem       Date:  2013-09-10       Impact factor: 4.354

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.  Asymmetric Synthesis of Axinellamines A and B.

Authors:  Zhiqiang Ma; Xiao Wang; Yuyong Ma; Chuo Chen
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-08       Impact factor: 15.336

Review 10.  Dimeric pyrrole-imidazole alkaloids: synthetic approaches and biosynthetic hypotheses.

Authors:  Xiao Wang; Zhiqiang Ma; Xiaolei Wang; Saptarshi De; Yuyong Ma; Chuo Chen
Journal:  Chem Commun (Camb)       Date:  2014-05-15       Impact factor: 6.222
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