Literature DB >> 21846138

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

Shun Su1, Rodrigo A Rodriguez, Phil S Baran.   

Abstract

The development of a simple, efficient, scalable, and stereocontrolled synthesis of a common intermediate en route to the axinellamines, massadines, and palau'amine is reported. This completely new route was utilized to prepare the axinellamines on a gram scale. In a more general sense, three distinct and enabling methodological advances were made during these studies: (1) an ethylene glycol-assisted Pauson-Khand cycloaddition reaction, (2) a Zn/In-mediated Barbier-type reaction, and (3) a TfNH(2)-assisted chlorination-spirocyclization.

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Year:  2011        PMID： 21846138      PMCID： PMC3164937          DOI： 10.1021/ja206191g

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  18 in total

Review 1.  The Pauson-Khand reaction, a powerful synthetic tool for the synthesis of complex molecules.

Authors:  Jaime Blanco-Urgoiti; Loreto Añorbe; Leticia Pérez-Serrano; Gema Domínguez; Javier Pérez-Castells
Journal:  Chem Soc Rev       Date:  2003-11-27       Impact factor: 54.564

2.  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

3.  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

4.  Massadine chloride: a biosynthetic precursor of massadine and stylissadine.

Authors:  Achim Grube; Stefan Immel; Phil S Baran; Matthias Köck
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  The pursuit of palau'amine.

Authors:  Matthias Köck; Achim Grube; Ian B Seiple; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

6.  Extending Pummerer reaction chemistry: studies in the palau'amine synthesis area.

Authors:  Ken S Feldman; Ahmed Yimam Nuriye; Jianfeng Li
Journal:  J Org Chem       Date:  2011-05-25       Impact factor: 4.354

7.  Revisiting the Kinnel-Scheuer hypothesis for the biosynthesis of palau'amine.

Authors:  Zhiqiang Ma; Jianming Lu; Xiao Wang; Chuo Chen
Journal:  Chem Commun (Camb)       Date:  2010-09-16       Impact factor: 6.222

8.  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

9.  Massadine, a novel geranylgeranyltransferase type I inhibitor from the marine sponge Stylissa aff. massa.

Authors:  Shinichi Nishimura; Shigeki Matsunaga; Mitsuyoshi Shibazaki; Kenichi Suzuki; Kazuo Furihata; Rob W M van Soest; Nobuhiro Fusetani
Journal:  Org Lett       Date:  2003-06-26       Impact factor: 6.005

10.  Total synthesis of palau'amine.

Authors:  Ian B Seiple; Shun Su; Ian S Young; Chad A Lewis; Junichiro Yamaguchi; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2010-02-01       Impact factor: 15.336
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  19 in total

Review 1.  Natural products as sources of new drugs over the 30 years from 1981 to 2010.

Authors:  David J Newman; Gordon M Cragg
Journal:  J Nat Prod       Date:  2012-02-08       Impact factor: 4.050

2.  Rapid access to the core skeleton of the [3 + 2]-type dimeric pyrrole-imidazole alkaloids by triplet ketone-mediated C-H functionalization.

Authors:  Lin You; Chuo Chen
Journal:  Tetrahedron       Date:  2017-12-15       Impact factor: 2.457

3.  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

4.  Metallacycle-Mediated Cross-Coupling in Natural Product Synthesis.

Authors:  Natasha F O'Rourke; Matthew J Kier; Glenn C Micalizio
Journal:  Tetrahedron       Date:  2016-09-07       Impact factor: 2.457

5.  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

6.  Syntheses of Cyclic Guanidine-Containing Natural Products.

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

7.  Catalytic enantioselective alkene aminohalogenation/cyclization involving atom transfer.

Authors:  Michael T Bovino; Sherry R Chemler
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-05       Impact factor: 15.336

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

10.  Stereocontrolled Formation of a [4.4]Heterospiro Ring System with Unexpected Inversion of Configuration at the Spirocenter.

Authors:  Zhiqiang Ma; Lin You; Chuo Chen
Journal:  J Org Chem       Date:  2016-12-20       Impact factor: 4.354
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