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Literature DB >> 20141121

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

Leslie N Aldrich¹, Eric S Dawson, Craig W Lindsley.

Abstract

The first synthetic efforts toward marineosins A and B, novel spiroaminals from a Streptomyces actinomycete, are described by evaluation of the proposed biosynthesis. The hypothesized biosynthetic C1-C25 Diels-Alder substrate was prepared in 8 steps in 5.1% overall yield; however, the proposed biomimetic inverse-electron-demand hetero-Diels-Alder reaction failed to deliver the marineosin core. Molecular mechanics supports this observation.

Entities: Chemical Species

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Year: 2010 PMID： 20141121 DOI： 10.1021/ol100034p

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

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Cited

12 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. Elimination of butylcycloheptylprodigiosin as a known natural product inspired by an evolutionary hypothesis for cyclic prodigiosin biosynthesis.

Authors: Brian T Jones; Dennis X Hu; Brett M Savoie; Regan J Thomson
Journal: J Nat Prod Date: 2013-09-20 Impact factor: 4.050

Review 10. Marine Pyrrole Alkaloids.

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

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

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

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

3. Elimination of butylcycloheptylprodigiosin as a known natural product inspired by an evolutionary hypothesis for cyclic prodigiosin biosynthesis.

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

5. Enantioselective synthesis of metacycloprodigiosin via the "Wasserman pyrrole".

6. Enantioselective total synthesis and confirmation of the absolute and relative stereochemistry of streptorubin B.

7. Modular access to complex prodiginines: total synthesis of (+)-roseophilin via its 2-azafulvene prototropisomer.

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

Review 9. Structure, Chemical Synthesis, and Biosynthesis of Prodiginine Natural Products.

Review 10. Marine Pyrrole Alkaloids.