792911-22-9Relevant academic research and scientific papers
Nhatrangin A: Total Syntheses of the Proposed Structure and Six of Its Diastereoisomers
Dias, Luiz C.,Polo, Ellen C.
, p. 4072 - 4112 (2017/04/28)
A total synthesis of the proposed structure of nhatrangin A is described. This strategy relies on two aldol reactions to install the chiral centers at C3/C4 and C3′/C4′, a lithium-mediated coupling between an advanced intermediate alkyne and a Weinreb amide to complete the C1-C13 alkyl scaffold, and a Yamaguchi esterification to set the side chain. Discrepancies in the spectroscopic data between synthetic and natural nhatrangins led us to synthesize six more diastereoisomers of the proposed structure of nhatrangin A.
Investigations of the stereoselectivity of the intramolecular Diels-Alder reaction of a spiculoic acid model system
Crossman, Julia S.,Perkins, Michael V.
, p. 4852 - 4867 (2008/09/21)
Model linear precursors to the spiculoic acids were prepared and underwent thermally induced IMDA reactions. The configuration of C5 in the stereotriad was found to dominate any inherent endo/exo selectivity of the IMDA reaction. The isomer (2E,5S)-20 underwent the IMDA to give the spiculoic acid stereochemistry in 84% yield and 94% ds. The required stereotriads were synthesised using stereoselective substrate-controlled aldol reactions; an anti-boron aldol reaction, controlled by the π-facial preference of (S)-2-benzoyloxypentan-3-one ((S)-27) led to (5R)-(22) and a syn-titanium aldol reaction, under the stereocontrol of a chiral N-acylthiazolidinethione (42) led to (5S)-(22). Chain extension using standard Wittig, HWE and 'modified' Julia olefinations installed the diene and dienophile components giving the linear precursors to the IMDA reactions.
Synthesis and biological evaluation of (-)-dictyostatin and stereoisomers
Shin, Youseung,Fournier, Jean-Hugues,Brückner, Arndt,Madiraju, Charitha,Balachandran, Raghavan,Raccor, Brianne S.,Edler, Michael C.,Hamel, Ernest,Sikorski, Rachel?P.,Vogt, Andreas,Day, Billy W.,Curran, Dennis P.
, p. 8537 - 8562 (2008/02/09)
Total syntheses of (-)-dictyostatin, 6,16-bis-epi-dictyostatin, 6,14,19-tris-epi-dictyostatin, and a number of other isomers and analogs are reported. Three main fragments-top, middle, and bottom-were first assembled and then joined by olefination or anio
ANALOGS OF DICTYOSTATIN, INTERMEDIATES THEREFOR AND METHODS OF SYNTHESIS THEREOF
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, (2008/06/13)
Dictyostatin and its analogs show great promise as new anticancer agents. The present invention provides dictyostatin analogs, synthetic intermediates for the synthesis of dictyostatin analogs, and synthetic methods for the synthesis of such analogs and i
METHODS FOR THE SYNTHESIS OF DICTYOSTATIN AND DERIVATIVES AND ANALOGUES THEREOF, STEREOCHEMICAL CHARACTERISATION, NOVEL DICTYOSTATIN COMPOUNDS AND USES THEREOF AND SYNTHETIC INTERMEDIATES
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Page/Page column 47-48; 147-148, (2010/02/13)
A method for the synthesis of dictyostatin or a derivative thereof having Formula (I) is provided.
Total synthesis and configurational assignment of (-)-dictyostatin, a microtubule-stabilizing macrolide of marine sponge origin
Paterson, Ian,Britton, Robert,Delgado, Oscar,Meyer, Arndt,Poullennec, Karine G.
, p. 4629 - 4633 (2007/10/03)
A flexible and modular approach was used in the convergent and highly stereocontrolled synthesis of the antimitotic agent dictyostatin. This first total synthesis establishes its full stereochemistry and should be amenable to producing useful quantities a
