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Literature DB >> 21327225

A stereoselective, Sm(II)-mediated approach to decorated cis-hydrindanes: synthetic studies on faurinone and pleuromutilin.

Thomas J K Findley¹, David Sucunza, Laura C Miller, Matthew D Helm, Madeleine Helliwell, David T Davies, David J Procter.

Abstract

The cis-hydrindane motif is found in a number of natural products that display important biological activity. A flexible, stereoselective approach to the framework has been developed that features highly diastereoselective, SmI(2)-mediated cyclisations. The strategy has been exploited in the first synthesis of the proposed structure of faurinone and an approach to the skeleton of the antibacterial natural product, pleuromutilin.

Entities: Chemical

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Year: 2011 PMID： 21327225 DOI： 10.1039/c0ob01086c

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

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Cited

8 in total

1. Diastereoselective syntheses of substituted cis-hydrindanones featuring sequential inter- and intramolecular Michael reactions.

Authors: Junjia Liu; Maurice A Marsini; T Aaron Bedell; Paul J Reider; Erik J Sorensen
Journal: Tetrahedron Date: 2016-03-15 Impact factor: 2.457

8. Copper-Catalyzed Double Additions and Radical Cyclization Cascades in the Re-Engineering of the Antibacterial Pleuromutilin.

Authors: Rebecca E Ruscoe; Neal J Fazakerley; Huanming Huang; Sabine Flitsch; David J Procter
Journal: Chemistry Date: 2015-11-26 Impact factor: 5.236

8 in total

A stereoselective, Sm(II)-mediated approach to decorated cis-hydrindanes: synthetic studies on faurinone and pleuromutilin.

1. Diastereoselective syntheses of substituted cis-hydrindanones featuring sequential inter- and intramolecular Michael reactions.

2. Development of a Modular Synthetic Route to (+)-Pleuromutilin, (+)-12-epi-Mutilins, and Related Structures.

3. Expanding the pleuromutilin class of antibiotics by de novo chemical synthesis.

4. A modular and enantioselective synthesis of the pleuromutilin antibiotics.

5. Scalable Synthesis of a Key Intermediate for the Production of Pleuromutilin-Based Antibiotics.

6. Design and Synthesis of Molecular Scaffolds with Anti-infective Activity.

7. Synthesis of cis-hydrindan-2,4-diones bearing an all-carbon quaternary center by a Danheiser annulation.

8. Copper-Catalyzed Double Additions and Radical Cyclization Cascades in the Re-Engineering of the Antibacterial Pleuromutilin.