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Literature DB >> 17854197

Improved biomimetic total synthesis of D,L-stephacidin A.

Abstract

The direct conversion of beta-hydroxyproline derivatives into 5-hydroxypyrazin-2(1H)-ones under Mitsunobu conditions has been discovered to be a general biomimetic protocol generating IMDA intermediates and has been applied to the concise, biomimetic total syntheses of D,L-stephacidin A and D,L-brevianamide B.

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 17854197 DOI： 10.1021/ol701845t

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

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Cited

20 in total

1. Studies Towards Paraherquamides E & F and Related C-labeled Putative Biosynthetic Intermediates: Stereocontrolled Synthesis of the α-Alkyl-β-Methylproline Ring System.

Authors: Konrad Sommer; Robert M Williams
Journal: Tetrahedron Date: 2008-07-21 Impact factor: 2.457

2. Intermolecular Diels-Alder Cycloaddition for the Construction of Bicyclo[2.2.2]diazaoctane Structures: Formal Synthesis of Brevianamide B and Premalbrancheamide.

Authors: Jacob G Robins; Kyu J Kim; Alex J Chinn; John S Woo; Jonathan R Scheerer
Journal: J Org Chem Date: 2016-02-26 Impact factor: 4.354

3. Studies on the Biosynthesis of the Stephacidin and Notoamide Natural Products: A Stereochemical and Genetic Conundrum.

Authors: James D Sunderhaus; David H Sherman; Robert M Williams
Journal: Isr J Chem Date: 2011-04 Impact factor: 3.333

Review 4. Synthetic approaches to the bicyclo[2.2.2]diazaoctane ring system common to the paraherquamides, stephacidins and related prenylated indole alkaloids.

Authors: Kenneth A Miller; Robert M Williams
Journal: Chem Soc Rev Date: 2009-09-16 Impact factor: 54.564

Improved biomimetic total synthesis of D,L-stephacidin A.

1. Studies Towards Paraherquamides E & F and Related C-labeled Putative Biosynthetic Intermediates: Stereocontrolled Synthesis of the α-Alkyl-β-Methylproline Ring System.

2. Intermolecular Diels-Alder Cycloaddition for the Construction of Bicyclo[2.2.2]diazaoctane Structures: Formal Synthesis of Brevianamide B and Premalbrancheamide.

3. Studies on the Biosynthesis of the Stephacidin and Notoamide Natural Products: A Stereochemical and Genetic Conundrum.

Review 4. Synthetic approaches to the bicyclo[2.2.2]diazaoctane ring system common to the paraherquamides, stephacidins and related prenylated indole alkaloids.

Review 5. Natural products synthesis: enabling tools to penetrate Nature's secrets of biogenesis and biomechanism.

6. Total synthesis of brevianamide A.

7. Calmodulin inhibitory activity of the malbrancheamides and various analogs.

8. Biomimetic total synthesis of malbrancheamide and malbrancheamide B.

9. Synthesis of functionalized indolizidines through Pauson-Khand cycloaddition of 2-allylpyrrolidines.

10. An improved synthesis of alpha,beta-unsaturated nitrones relevant to the stephacidins and analogs thereof.