Literature DB >> 23606772

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

Joseph D Panarese1, Leah C Konkol, Cynthia B Berry, Brittney S Bates, Leslie N Aldrich, Craig W Lindsley.   

Abstract

In this Letter, we describe a short, 6-step enantioselective route to spiroaminal lactam model systems reminiscent of marineosins A and B has been developed starting from either (R)- or (S)-hydroxysuccinic acid, respectively, in ~9% overall yield. This route enables late stage incorporation of the pyrrole ring at C5 via nucleophilic displacement of an iminium triflate salt.

Entities:  

Keywords:  alkaloid; enantioselective; iminium triflate; marineosin; pyrrole

Year:  2013        PMID： 23606772      PMCID： PMC3627418          DOI： 10.1016/j.tetlet.2013.02.059

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


  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.  Total synthesis and biological evaluation of tambjamine K and a library of unnatural analogs.

Authors:  Leslie N Aldrich; Sydney L Stoops; Brenda C Crews; Lawrence J Marnett; Craig W Lindsley
Journal:  Bioorg Med Chem Lett       Date:  2010-07-23       Impact factor: 2.823

3.  Synthesis of the spiroiminal moiety of marineosins A and B.

Authors:  Xiao-Chuan Cai; Xiaoxing Wu; Barry B Snider
Journal:  Org Lett       Date:  2010-04-02       Impact factor: 6.005

4.  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

5.  Influence of the a-ring on the redox and nuclease properties of the prodigiosins: importance of the bipyrrole moiety in oxidative DNA cleavage.

Authors:  Matt S Melvin; M Wade Calcutt; Ronald E Noftle; Richard A Manderville
Journal:  Chem Res Toxicol       Date:  2002-05       Impact factor: 3.739

6.  4-[(Alkylamino)methyl]furo[3,2-c]pyridines: a new series of selective kappa-receptor agonists.

Authors:  A Naylor; D B Judd; D I Scopes; A G Hayes; P J Birch
Journal:  J Med Chem       Date:  1994-07-08       Impact factor: 7.446

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
  5 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

Review 4.  Marine Pyrrole Alkaloids.

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

5.  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
  5 in total

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