212703-47-4Relevant academic research and scientific papers
Large-Scale Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide. Part 2: Synthesis of Fragments C1-6 and C 9-14
Mickel, Stuart J.,Sedelmeier, Gottfried H.,Niederer, Daniel,Schuerch, Friedrich,Grimler, Dominique,Koch, Guido,Daeffler, Robert,Osmani, Adnan,Hirni, Alfred,Schaer, Karl,Gamboni, Remo,Bach, Andrew,Chaudhary, Apurva,Chen, Stephen,Chen, Weichun,Hu, Bin,Jagoe, Christopher T.,Kim, Hong-Yong,Kinder Jr., Frederick R.,Liu, Yugang,Lu, Yansong,McKenna, Joseph,Prashad, Mahavir,Ramsey, Timothy M.,Repic, Oljan,Rogers, Larry,Shieh, Wen-Chung,Wang, Run-Ming,Waykole, Liladhar
, p. 101 - 106 (2004)
Kilogram-scale syntheses of fragments C1-6 (6) and C 9-14 (4) of (+)-discodermolide from common precursor 3 are described. Improved procedures for each step of both fragments were developed by minimizing or eliminating the formation
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.
Leptolyngbyolides, Cytotoxic Macrolides from the Marine Cyanobacterium Leptolyngbya sp.: Isolation, Biological Activity, and Catalytic Asymmetric Total Synthesis
Cui, Jin,Morita, Maho,Ohno, Osamu,Kimura, Tomoyuki,Teruya, Toshiaki,Watanabe, Takumi,Suenaga, Kiyotake,Shibasaki, Masakatsu
, p. 8500 - 8509 (2017/06/28)
Four new macrolactones, leptolyngbyolides A–D, were isolated from the cyanobacterium Leptolyngbya sp. collected in Okinawa, Japan. The planar structures of leptolyngbyolides were determined by extensive NMR studies, although complete assignment of the abs
Synthesis of the C11-C23 fragment of the potent antitumor agent dlctyostatin
Dias, Luiz C.,Lima, Dimas J.P.,Goncalves, Caroline C.S.,Andricopulo, Adriano D.
supporting information; experimental part, p. 1491 - 1494 (2009/07/11)
We wish to report here our initial efforts toward the total synthesis of the potent antitumor agent dlctyostatin, describing a short and efficient synthesis of the C11-C23 fragment. Wiley-VCH Verlag GmbH & Co. KGaA.
Total synthesis of pteridic acids A and B
Dias, Luiz C.,Salles Jr., Airton G.
scheme or table, p. 5584 - 5589 (2009/12/03)
(Chemical Equation Presented) The total synthesis of pteridic acids A and B is reported. The convergent asymmetric synthesis involved the use of a diastereoselective ethyl ketone aldol reaction followed by an efficient spiroketalization and provided pteri
Two-directional total synthesis of efomycine M and formal total synthesis of elaiolide
Barth, Roland,Mulzer, Johann
, p. 4718 - 4735 (2008/09/21)
The anti-inflammatory agent efomycine M (1) has been synthesized from macrodilactone 38 and vinyliodide 42 by a two-directional total synthesis in 17 steps over the longest linear sequence with an overall yield of 7%. The C2-symmetric macrodiolide 38 has been prepared by Yamaguchi macrolactonization of seco-acid 26. The central stereopentad of 1 was obtained by a highly efficient anti-aldol reaction followed by a diastereoselective ketone reduction. Additionally, we have completed a formal total synthesis of elaiolide (3) by converting macrodiolide 37 into Paterson's methylketone 13.
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
Synthesis and biological evaluation of (-)-16-normethyldictyostatin: A potent analogue of (-)-dictyostatin
Shin, Youseung,Fournier, Jean-Hugues,Balachandran, Raghavan,Madiraju, Charitha,Raccor, Brianne S.,Zhu, Guangyu,Edler, Michael C.,Hamel, Ernest,Day, Billy W.,Curran, Dennis P.
, p. 2873 - 2876 (2007/10/03)
(Chemical Equation Presented) (-)-16-Normethyldictyostatin has been made by total synthesis and is a potent antitumor agent in cells expressing wild-type tubulin and in one mutant cell line that is resistant to paclitaxel, but it is much less active than
Bio-intermediates for use in the chemical synthesis of polyketides
-
, (2008/06/13)
The present invention relates to compounds made by a subset of modules from one or more polyketide synthase (“PKS”) genes that are used as starting material in the chemical synthesis of novel molecules, particularly naturally occurring polyketides or deri
