118949-49-8Relevant academic research and scientific papers
Total Synthesis of Pericoannosin A
Lücke, Daniel,Linne, Yannick,Hempel, Katharina,Kalesse, Markus
, p. 4475 - 4477 (2018)
The first total synthesis of pericoannosin A (1) containing 15 steps in the longest linear sequence with an overall yield of 5.5% is reported. The hybrid peptide-polyketide was isolated from the endophytic fungus Periconia sp. F-31 and bears a unique tric
An RCM-Based Total Synthesis of the Antibiotic Disciformycin B
Altmann, Karl-Heinz,Waser, Philipp
supporting information, p. 17393 - 17397 (2020/08/14)
The total synthesis of the potent new antibiotic disciformycin B (2) is described, which shows significant activity against methicillin- and vancomycin-resistant Staphylococcus aureus (MRSA/VRSA) strains. The synthetic route is based on macrocyclization o
Spirastrellolide E: Synthesis of an advanced C(1)-C(24) southern hemisphere
Sokolsky, Alexander,Wang, Xiaozhao,Smith, Amos B.
supporting information, p. 3160 - 3164 (2015/03/04)
The synthesis of a C(1)-C(24) advanced southern hemisphere fragment towards the total synthesis of spirastrellolide E has been achieved. Highlights of the route include a highly convergent Type I Anion Relay Chemistry (ARC) tactic for fragment assembly, in conjunction with a directed, regioselective gold-catalyzed alkyne functionalization to generate the central unsaturated [6,6]-spiroketal.
The stereocontrolled total synthesis of spirastrellolide A methyl ester. Expedient construction of the key fragments
Paterson, Ian,Anderson, Edward A.,Dalby, Stephen M.,Lim, Jong Ho,Maltas, Philip,Loiseleur, Olivier,Genovino, Julien,Moessner, Christian
, p. 5861 - 5872 (2012/08/28)
Due to a combination of their promising anticancer properties, limited supply from the marine sponge source and their unprecedented molecular architecture, spirastrellolides represent attractive and challenging synthetic targets. A modular strategy for the synthesis of spirastrellolide A methyl ester, which allowed for the initial stereochemical uncertainties in the assigned structure was adopted, based on the envisaged sequential coupling of a series of suitably functionalised fragments; in this first paper, full details of the synthesis of these fragments are described. The pivotal C26-C40 DEF bis-spiroacetal was assembled by a double Sharpless asymmetric dihydroxylation/acetalisation cascade process on a linear diene intermediate, configuring the C31 and C35 acetal centres under suitably mild acidic conditions. A C1-C16 alkyne fragment was constructed by application of an oxy-Michael reaction to introduce the A-ring tetrahydropyran, a Sakurai allylation to install the C9 hydroxyl, and a 1,4-syn boron aldol/directed reduction sequence to establish the C11 and C13 stereocentres. Two different coupling strategies were investigated to elaborate the C26-C40 DEF fragment, involving either a C17-C25 sulfone or a C17-C24 vinyl iodide, each of which was prepared using an Evans glycolate aldol reaction. The remaining C43-C47 vinyl stannane fragment required for introduction of the unsaturated side chain was prepared from (R)-malic acid.
Towards a simplified peloruside A: Synthesis of C1-C11 of a dihydropyran analogue
Casey, Emma M.,Tho, Febly,Harvey, Joanne E.,Teesdale-Spittle, Paul H.
experimental part, p. 9376 - 9381 (2011/12/03)
A simplified analogue of the C1-C11 fragment of peloruside A has been synthesised starting from a monoprotected 2,2-dimethylpropane-1,3-diol. Oxidation, asymmetric allylation and acryloylation provided a substrate for ring-closing metathesis to a δ-lacton
