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T1 - Total synthesis of (±)-platencin

A total synthesis of the potent antibacterial agent platencin is described. The reaction sequence used involves, as starting material, an enantiomerically pure -1,2-dihydrocatechol derived from the whole-cell biotransformation of iodobenzene. Simple chemical manipulations of this metabolite provide a triene that engages in a thermally promoted intramolecular Diels–Alder reaction to establish the octa­hydro-2-2,4a-ethanonaphthalene core of platencin.

Total Synthesis of (+)-Aspergillin PZ []

Our total synthesis endeavors toward platencin, first as a racemate, and then in its enantiomerically pure form, proceeded through a number of phases and evolved into a highly efficient and streamlined process. Below we describe these studies in approximately the chronological sequence they occurred.

Total synthesis of (±)-platencin — Okayama University

Part 1: Synthesis of key intermediates and intelligence gathering. 38:1669-1675.

ft., former Hercules/PFW facility in Middletown, NY; Fleurchem produces a full range of natural isolates, synthetic chemicals & specialities, essential oils and flavors.

A difficulty associated with this approach was the limited amount of intermediate available by such means. Furthermore, introducing the required C4 methyl and propionic acid groups in an efficient and stereocontrolled manner proved problematic. In an attempt to address these issues, we recently reported[] an alternate IMDA-based approach that delivered a more highly functionalised form of compound and one that could be converted, over a further thirteen steps, into platencin. However, significant functional group incompatibilities were encountered in this first chemoenzymatic total synthesis of the title natural product. Given the deficiencies associated with both of our previous routes we pursued a second-generation chemoenzymatic total synthesis. As a result, we have established, and now report, a more concise as well as a regio- and stereocontrolled pathway to compound that exploits key elements of our earlier approach to enone .

Total synthesis of platencin. - F1000Prime

Total Synthesis of the Anti-Leukemia Alkaloid (-)-Deoxyharringtonine [] Zhiyong: Total Synthesis of Iejimalide B

Fatty acid biosynthesis, an essential process for the survival and propagation of bacteria, is the primary means by which bacteria form fatty acids necessary for energy storage and cellular structure building blocks. This, along with the significant differences between the human and bacterial fatty acid biosynthetic machinery, makes the bacterial fatty acid synthase (FAS) pathway an attractive strategy in the against drug-resistant bacteria., Taking advantage of modern biological techniques, a Merck team recently developed an antisense silencing RNA based assay for identifying inhibitors of the type II fatty acid biosynthesis (FAS II) pathway present in bacterial cells. The gene encoding the FabH and FabF condensing enzymes of FAS II was silenced, sensitizing the bacteria to inhibitors of these enzymes, and allowing for a high-throughput, whole cell, target-based assay. Screening of 250,000 natural product extracts ultimately led to the discovery of the dual FabF/FabH inhibitor platencin (1) and its congener platencin A1, along with the selective FabF inhibitor platensimycin (2).

The secondary metabolites platensimycin (1) and platencin (2), isolated from the bacterial strain Streptomyces platensis, represent a novel class of natural products exhibiting unique and potent antibacterial activity. Platencin, though structurally similar to platensimycin, has been found to operate through a slightly different mechanism of action involving the dual inhibition of lipid elongation enzymes FabF and FabH. Both natural products exhibit strong, broad-spectrum, Gram-positive antibacterial activity to key antibiotic resistant strains, including methicillin-resistant Staphylococcus aureus, vancomycin-intermediate S. aureus, and vancomycin-resistant Enterococcus faecium. Described herein are our synthetic efforts toward platencin, culminating in both the racemic and asymmetric preparation of the natural product. The syntheses demonstrate the power of the cobalt-catalyzed asymmetric Diels–Alder reaction and the one-pot reductive rearrangement of [3.2.1] bicyclic ketones to [2.2.2] bicyclic olefins.

Total Synthesis in Year 2008
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Total Synthesis of (±)-Platencin

A total synthesis of the potent antibacterial agent platencin is described. The reaction sequence used involves, as starting material, an enantiomerically pure -1,2-dihydrocatechol derived from the whole-cell biotransformation of iodobenzene. Simple chemical manipulations of this metabolite provide a triene that engages in a thermally promoted intramolecular Diels–Alder reaction to establish the octa­hydro-2-2,4a-ethanonaphthalene core of platencin.

NNNS chemistry blog: Codeine total synthesis …

This Letter describes an enantioselective approach to (-)-platencin. A uniquely functionalized chiral intermediate, which was prepared via the highly enantioselective catalytic asymmetric intramolecular cyclopropanation (CAIMCP) that we have developed, was successfully transformed to Nicolaou's intermediate in his total synthesis of (-)-platencin.

Total Synthesis of Codeine by Magnus - Organic chemistry

N2 - This Letter describes an enantioselective approach to (-)-platencin. A uniquely functionalized chiral intermediate, which was prepared via the highly enantioselective catalytic asymmetric intramolecular cyclopropanation (CAIMCP) that we have developed, was successfully transformed to Nicolaou's intermediate in his total synthesis of (-)-platencin.

Total Synthesis of Codeine Magnus

AB - This Letter describes an enantioselective approach to (-)-platencin. A uniquely functionalized chiral intermediate, which was prepared via the highly enantioselective catalytic asymmetric intramolecular cyclopropanation (CAIMCP) that we have developed, was successfully transformed to Nicolaou's intermediate in his total synthesis of (-)-platencin.

Asymmetric total synthesis of (−)-melotenine A

Extensive screening over 250,000 natural product extracts has led to the discovery of platencin and platensimycin with a novel chemical scaffold from strains of Streptomyces platensis. Platencin blocks two essential proteins for bacterial fatty acid biosynthesis, beta-ketoacyl-acyl carrier protein (ACP) synthase II (FabF) and III (FabH), whereas platensimycin selectively inhibits FabF. Due to their unique mode of action, both compounds have caught considerable attention as new potent antibiotics capable of combating antibiotic resistant strains such as methicillin-resistant Staphylococcus aureus (MRSA). Here, a new approach to the platencin motif is reported, in which titanocene(III) chloride-mediated radical cyclization and allyl-homoallyl radical rearrangement reactions are utilized to furnish a highly fused tricyclic compound with all the requisite functionalities and stereochemistry for total synthesis.

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