Literature DB >> 20218641

Synthesis of the spiroiminal moiety of marineosins A and B.

Xiao-Chuan Cai1, Xiaoxing Wu, Barry B Snider.   

Abstract

A model for the spiroiminal moiety of marineosins A and B was prepared starting from methylvalerolactone. Addition of vinylmagnesium bromide, protection of the alcohol, and reaction of the vinyl ketone with a protected pyrrole-2-carbonitrile N-oxide gave an isoxazoline. Hydrogenolysis of the N-O bond with Raney nickel gave a keto imine that cyclized to a hemi-iminal. O-Methylation, acid-catalyzed cleavage of the TES group and spiroiminal formation, and deprotection completed a seven-step synthesis.

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Year:  2010        PMID： 20218641      PMCID： PMC2877921          DOI： 10.1021/ol100333d

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 in total

Review 1.  Chemistry and biology of roseophilin and the prodigiosin alkaloids: a survey of the last 2500 years.

Authors:  Alois Fürstner
Journal:  Angew Chem Int Ed Engl       Date:  2003-08-11       Impact factor: 15.336

2.  Evaluation of the biosynthetic proposal for the synthesis of marineosins A and B.

Authors:  Leslie N Aldrich; Eric S Dawson; Craig W Lindsley
Journal:  Org Lett       Date:  2010-03-05       Impact factor: 6.005

3.  Analysis of the prodiginine biosynthesis gene cluster of Streptomyces coelicolor A3(2): new mechanisms for chain initiation and termination in modular multienzymes.

Authors:  A M Cerdeño; M J Bibb; G L Challis
Journal:  Chem Biol       Date:  2001-08

Review 4.  The biosynthesis and regulation of bacterial prodiginines.

Authors:  Neil R Williamson; Peter C Fineran; Finian J Leeper; George P C Salmond
Journal:  Nat Rev Microbiol       Date:  2006-12       Impact factor: 60.633

5.  Elucidation of the Streptomyces coelicolor pathway to 2-undecylpyrrole, a key intermediate in undecylprodiginine and streptorubin B biosynthesis.

Authors:  SangJoon Mo; Paulina K Sydor; Christophe Corre; Mamoun M Alhamadsheh; Anna E Stanley; Stuart W Haynes; Lijiang Song; Kevin A Reynolds; Gregory L Challis
Journal:  Chem Biol       Date:  2008-02

6.  Anticancer and immunosuppressive properties of bacterial prodiginines.

Authors:  Neil R Williamson; Peter C Fineran; Tamzin Gristwood; Suresh R Chawrai; Finian J Leeper; George P C Salmond
Journal:  Future Microbiol       Date:  2007-12       Impact factor: 3.165

7.  Marineosins A and B, cytotoxic spiroaminals from a marine-derived actinomycete.

Authors:  Chollaratt Boonlarppradab; Christopher A Kauffman; Paul R Jensen; William Fenical
Journal:  Org Lett       Date:  2008-12-18       Impact factor: 6.005
  7 in total
  8 in total

1.  Towards the Total Synthesis of Marineosin A: Construction of the Macrocyclic Pyrrole and an Advanced, Functionalized Spiroaminal Model.

Authors:  Leslie N Aldrich; Cynthia B Berry; Brittney S Bates; Leah C Konkol; Miranda So; Craig W Lindsley
Journal:  European J Org Chem       Date:  2013-07-01

2.  MarH, a Bifunctional Enzyme Involved in the Condensation and Hydroxylation Steps of the Marineosin Biosynthetic Pathway.

Authors:  Wanli Lu; Papireddy Kancharla; Kevin A Reynolds
Journal:  Org Lett       Date:  2017-03-08       Impact factor: 6.005

3.  Synthesis of the spiroiminal moiety and approaches to the synthesis of marineosins A and B.

Authors:  Xiao-Chuan Cai; Barry B Snider
Journal:  J Org Chem       Date:  2013-11-21       Impact factor: 4.354

4.  Spiroaminal Model Systems of the Marineosins with Final Step Pyrrole Incorporation.

Authors:  Joseph D Panarese; Leah C Konkol; Cynthia B Berry; Brittney S Bates; Leslie N Aldrich; Craig W Lindsley
Journal:  Tetrahedron Lett       Date:  2013-05-01       Impact factor: 2.415

Review 5.  Structure, Chemical Synthesis, and Biosynthesis of Prodiginine Natural Products.

Authors:  Dennis X Hu; David M Withall; Gregory L Challis; Regan J Thomson
Journal:  Chem Rev       Date:  2016-06-17       Impact factor: 60.622

Review 6.  Marine Pyrrole Alkaloids.

Authors:  Kevin Seipp; Leander Geske; Till Opatz
Journal:  Mar Drugs       Date:  2021-09-10       Impact factor: 5.118

7.  Stereospecific synthesis of 23-hydroxyundecylprodiginines and analogues and conversion to antimalarial premarineosins via a Rieske oxygenase catalyzed bicyclization.

Authors:  Papireddy Kancharla; Wanli Lu; Shaimaa M Salem; Jane Xu Kelly; Kevin A Reynolds
Journal:  J Org Chem       Date:  2014-11-18       Impact factor: 4.354

8.  Elucidation of final steps of the marineosins biosynthetic pathway through identification and characterization of the corresponding gene cluster.

Authors:  Shaimaa M Salem; Papireddy Kancharla; Galina Florova; Shweta Gupta; Wanli Lu; Kevin A Reynolds
Journal:  J Am Chem Soc       Date:  2014-03-12       Impact factor: 15.419
  8 in total

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