Literature DB >> 23929596

A synthesis of the chlorosulfolipid mytilipin A via a longest linear sequence of seven steps.

Won-Jin Chung1, Joseph S Carlson, D Karl Bedke, Christopher D Vanderwal.   

Abstract

Magnificent seven: The chlorosulfolipid mytilipin A was synthesized in racemic form in seven steps and in enantioenriched form in eight steps. Key transformations include a highly diastereoselective bromoallylation of a sensitive α,β-dichloroaldehyde, a kinetic resolution of a vinyl epoxide, a convergent and highly Z-selective alkene cross-metathesis, and a chemoselective and diastereoselective dichlorination of a complex diene.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  kinetic resolution; lipids; metathesis; natural products; total synthesis

Mesh:

Substances:

Year:  2013        PMID: 23929596      PMCID: PMC3835569          DOI: 10.1002/anie.201304565

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  28 in total

1.  Synthesis of undecachlorosulfolipid A: re-evaluation of the nominal structure.

Authors:  Christian Nilewski; Nicholas R Deprez; Thomas C Fessard; Dong Bo Li; Roger W Geisser; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-08       Impact factor: 15.336

Review 2.  Chlorosulfolipids: structure, synthesis, and biological relevance.

Authors:  D Karl Bedke; Christopher D Vanderwal
Journal:  Nat Prod Rep       Date:  2010-12-02       Impact factor: 13.423

3.  Enantioselective dichlorination of allylic alcohols.

Authors:  K C Nicolaou; Nicholas L Simmons; Yongcheng Ying; Philipp M Heretsch; Jason S Chen
Journal:  J Am Chem Soc       Date:  2011-05-10       Impact factor: 15.419

4.  Total synthesis of a chlorosulpholipid cytotoxin associated with seafood poisoning.

Authors:  Christian Nilewski; Roger W Geisser; Erick M Carreira
Journal:  Nature       Date:  2009-01-29       Impact factor: 49.962

Review 5.  α-Haloaldehydes: versatile building blocks for natural product synthesis.

Authors:  Robert Britton; Baldip Kang
Journal:  Nat Prod Rep       Date:  2013-02       Impact factor: 13.423

6.  Microbial sulpholipids: (R)-13-choro-1-(R)-14-docosanediol disulphate and polychlorosulpholipids in Ochromonas danica.

Authors:  T H Haines; M Pousada; B Stern; G L Mayers
Journal:  Biochem J       Date:  1969-07       Impact factor: 3.857

7.  Structure revision and absolute configuration of malhamensilipin A from the freshwater chrysophyte Poterioochromonas malhamensis.

Authors:  Alban R Pereira; Tara Byrum; Grant M Shibuya; Christopher D Vanderwal; William H Gerwick
Journal:  J Nat Prod       Date:  2010-02-26       Impact factor: 4.050

8.  Stereoselective dichlorination of allylic alcohol derivatives to access key stereochemical arrays of the chlorosulfolipids.

Authors:  Grant M Shibuya; Jacob S Kanady; Christopher D Vanderwal
Journal:  J Am Chem Soc       Date:  2008-08-22       Impact factor: 15.419

9.  Enantioselective total synthesis of (-)-napyradiomycin A1 via asymmetric chlorination of an isolated olefin.

Authors:  Scott A Snyder; Zhen-Yu Tang; Ritu Gupta
Journal:  J Am Chem Soc       Date:  2009-04-29       Impact factor: 15.419

10.  Catalytic Z-selective olefin cross-metathesis for natural product synthesis.

Authors:  Simon J Meek; Robert V O'Brien; Josep Llaveria; Richard R Schrock; Amir H Hoveyda
Journal:  Nature       Date:  2011-03-24       Impact factor: 49.962

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  11 in total

1.  Organoselenium-catalyzed enantioselective syn-dichlorination of unbiased alkenes.

Authors:  Bradley B Gilbert; Stanley T-C Eey; Pavel Ryabchuk; Olivia Garry; Scott E Denmark
Journal:  Tetrahedron       Date:  2019-06-01       Impact factor: 2.457

2.  Approaches to the chemical synthesis of the chlorosulfolipids.

Authors:  Won-Jin Chung; Christopher D Vanderwal
Journal:  Acc Chem Res       Date:  2014-01-08       Impact factor: 22.384

3.  Ru-Based Z-Selective Metathesis Catalysts with Modified Cyclometalated Carbene Ligands.

Authors:  Sarah M Bronner; Myles B Herbert; Paresma R Patel; Vanessa M Marx; Robert H Grubbs
Journal:  Chem Sci       Date:  2014-10       Impact factor: 9.825

4.  Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A.

Authors:  Matthew L Landry; Dennis X Hu; Grace M McKenna; Noah Z Burns
Journal:  J Am Chem Soc       Date:  2016-04-08       Impact factor: 15.419

5.  Triphosgene-pyridine mediated stereoselective chlorination of acyclic aliphatic 1,3-diols.

Authors:  Andrés Villalpando; Mirza A Saputra; Thomas H Tugwell; Rendy Kartika
Journal:  Chem Commun (Camb)       Date:  2015-10-18       Impact factor: 6.222

Review 6.  Stereoselective Halogenation in Natural Product Synthesis.

Authors:  Won-jin Chung; Christopher D Vanderwal
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-02       Impact factor: 15.336

7.  Enantioselective divergent syntheses of several polyhalogenated Plocamium monoterpenes and evaluation of their selectivity for solid tumors.

Authors:  Carl V Vogel; Halina Pietraszkiewicz; Omar M Sabry; William H Gerwick; Frederick A Valeriote; Christopher D Vanderwal
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-12       Impact factor: 15.336

Review 8.  The Recurring Roles of Chlorine in Synthetic and Biological Studies of the Lissoclimides.

Authors:  Bonnie S Pak; Nantamon Supantanapong; Christopher D Vanderwal
Journal:  Acc Chem Res       Date:  2021-02-05       Impact factor: 22.384

9.  Ruthenium-catalysed Z-selective cross metathesis of allylic-substituted olefins.

Authors:  Brendan L Quigley; Robert H Grubbs
Journal:  Chem Sci       Date:  2014-02       Impact factor: 9.825

10.  General approach to the synthesis of the chlorosulfolipids danicalipin A, mytilipin A, and malhamensilipin A in enantioenriched form.

Authors:  Won-jin Chung; Joseph S Carlson; Christopher D Vanderwal
Journal:  J Org Chem       Date:  2014-02-13       Impact factor: 4.354

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