790661-41-5Relevant academic research and scientific papers
Stereoselective synthesis of maresin 1
Tungen, J?rn E.,Aursnes, Marius,Hansen, Trond Vidar
supporting information, p. 1843 - 1846 (2015/03/30)
Maresin 1 is a potent anti-inflammatory and pro-resolving lipid mediator derived from docosahexaenoic acid. The total synthesis of maresin 1 is achieved in 10 steps and in 7% overall yield. The Evans-Nagao aldol reaction between (2E,4E)-5-bromopenta-2,4-dienal and different chiral auxiliaries is investigated. The reported synthesis is efficient and highly stereoselective, affording multi-milligram quantities of this biologically interesting lipid mediator.
Stereoselective synthesis of protectin D1: A potent anti-inflammatory and proresolving lipid mediator
Aursnes,Tungen,Vik,Dalli,Hansen
supporting information, p. 432 - 437 (2014/01/06)
A convergent stereoselective synthesis of the potent anti-inflammatory, proresolving and neuroprotective lipid mediator protectin D1 (2) has been achieved in 15% yield over eight steps. The key features were a stereocontrolled Evans-aldol reaction with Nagao's chiral auxiliary and a highly selective Lindlar reduction of internal alkyne 23, allowing the sensitive conjugated E,E,Z-triene to be introduced late in the preparation of 2. The UV and LC/MS-MS data of synthetic protectin D1 (2) matched those obtained from endogenously produced material.
Total synthesis and structural validation of cyclodepsipeptides solonamide A and B
Kitir, Betül,Baldry, Mara,Ingmer, Hanne,Olsen, Christian A.
, p. 7721 - 7732 (2014/12/10)
Microorganisms are an attractive source of new natural products with antimicrobial properties, and the marine environment constitutes a prolific resource of bioactive microorganisms. During a global research expedition (Galathea III), two depsipeptides, solonamide A and solonamide B, were isolated from the marine bacterium Photobacterium halotolerance and were found to inhibit virulence gene expression in the serious human pathogen, Staphylococcus aureus. They act by interfering with the agr quorum sensing system and show resemblance to the endogenous S. aureus quorum sensing peptide, autoinducing peptide I (AIP-I). To enable more comprehensive studies, we embarked on the chemical synthesis of solonamides A and B. The key synthetic steps were formation of the (R)-β-hydroxy-fatty-acids by stereo-selective aldol reactions and a cyclative macrolactamization, which proceeded under highly dilute conditions. Thus, the first total syntheses of the solonamides corroborated the originally assigned structures, and by changing the stereochemistry of the auxiliary in the aldol steps we gained access to the natural products as well as their β3-epimers.
A concise stereoselective total synthesis of herbarumin III
Yadav, Jhillu S.,Kumar, Veerjala Naveen,Rao, Ramisetti Srinivasa,Srihari, Pabbaraja
experimental part, p. 1938 - 1942 (2009/04/04)
A stereoselective total Synthesis of the phytotoxic compound herbarumin III has been achieved by utilizing Crimmins's aldol approach, 1,3-syn asymmetric reduction, and an olefin metathesis reaction as the key steps.
Synthesis of the macrocyclic core of (-)-pladienolide B
Skaanderup, Philip R.,Jensen, Thomas
supporting information; experimental part, p. 2821 - 2824 (2009/05/27)
(Chemical Equation Presented) An efficient synthesis of the macrocyclic core of (-)-pladienolide B is disclosed. The concise route relies on a chiral auxiliary-mediated asymmetric aldol addition and an osmium-catalyzed asymmetric dihydroxylation to install the three oxygenated stereocenters of the macrocycle. This purely reagent-controlled and flexible strategy sets the stage for future analogue syntheses and structure-activity relationship plotting of the appealing anticancer lead structure pladienolide B.
