132969-60-9Relevant academic research and scientific papers
Synthesis of 12-aza analogs of epothilones and (E)-9,10-dehydroepothilones
Feyen, Fabian,Jantsch, Andrea,Hauenstein, Kurt,Pfeiffer, Bernhard,Altmann, Karl-Heinz
, p. 7920 - 7928 (2008)
N-Boc-12-aza-epothilone analog (azathilone) 1 is a potent inhibitor of human cancer cell growth and represents a structurally new class of natural product-derived microtubule-stabilizing agents. Compound 1 has been prepared employing a convergent strategy
Synthetic studies toward the total synthesis of tautomycetin
Pereira De Sant'Ana, Danilo,De Oliveira Rezende Júnior, Celso,Campagne, Jean-Marc,Dias, Luiz Carlos,Marcia De Figueiredo, Renata
, p. 12344 - 12357 (2019/10/10)
The studies culminating in the synthesis of two large subunits of tautomycetin are described. The first one, fragment C1-C12 that has an anti-1,3-dimethyl system and a terminal diene unit, was accomplished in 10 linear steps in 7.4% overall yield. The second one, fragment C13-C25 which bears the sensitive anhydride framework and the majority of the stereogenic centers, was prepared in 13 linear steps (longest sequence) in 8% overall yield. Among the key transformations used, a regioselective epoxide opening, a Pd-catalyzed addition of terminal alkyne to acceptor alkyne, a Mukaiyama aldol reaction, a Yamaguchi esterification, and a homemade mild di-esterification can be cited. The chosen strategies allowed good yields, stereoselectivity, reproducibility, and scalability for several important intermediates.
Stereoselective Synthesis of the C1-C22 Carbon Framework of (-)-Amphidinolide K
Chandankar, Somnath S.,Raghavan, Sadagopan
, p. 9584 - 9602 (2019/09/06)
Two stereoselective routes to the C7-C22 subunit of amphidinolide K are disclosed. Jacobsen's hydrolytic kinetic resolution and Sharpless' asymmetric dihydroxylation reactions have been employed for the construction of the tetrahydrofuran ring. The C10-C1
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.
Formal synthesis of tirandamycin B
Takahashi, Keisuke,Harada, Rintaro,Hoshino, Yurika,Kusakabe, Taichi,Hatakeyama, Susumi,Kato, Keisuke
, p. 3548 - 3553 (2017/06/01)
A formal synthesis of tirandamycin B is described. The key intermediate is synthesized by Marshall allenyl zinc method, litiofuran coupling, and Achmatowicz reaction to construct the bicyclic core of tirandamycin B.
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
Enantioselective Hydroformylation of 1-Alkenes with Commercial Ph-BPE Ligand
Yu, Zhiyong,Eno, Meredith S.,Annis, Alexandra H.,Morken, James P.
, p. 3264 - 3267 (2015/07/15)
A rhodium complex, in conjunction with commercially available Ph-BPE ligand, catalyzes the branch-selective asymmetric hydroformylation of 1-alkenes and rapidly generates α-chiral aldehydes. A wide range of terminal olefins including 1-dodecene were examined, and all delivered high enantioselectivity (up to 98:2 er) as well as good branch:linear ratios (up to 15:1). (Chemical Equation Presented).
Synthetic Studies toward the C32-C46 Segment of Hemicalide. Assignment of the Relative Configuration of the C36-C42 Subunit
Specklin, Simon,Boissonnat, Guillaume,Lecourt, Camille,Sorin, Geoffroy,Lannou, Marie-Isabelle,Ardisson, Janick,Sautel, Fran?ois,Massiot, Georges,Meyer, Christophe,Cossy, Janine
supporting information, p. 2446 - 2449 (2015/05/27)
The synthesis of five diastereomeric model compounds incorporating the C32-C46 segment of the antitumor marine natural product hemicalide has been achieved through a convergent approach relying on the 1,4-addition of an alkenyl boronate to an α,β-unsaturated δ-lactone followed by α-hydroxylation of an enolate and a Julia-Kocienski olefination. Comparison of the 1H and 13C NMR data of the model compounds with those of hemicalide enabled the assignment of the relative configuration of the C36-C42 subunit. (Chemical Equation Presented).
Studies toward the Total Synthesis of Tianchimycins A and B: Construction of the Complete C1-C16 Framework
Ankireddy, Sandeep,Ankireddy, Praveen,Sabitha, Gowravaram
, p. 2860 - 2868 (2015/09/15)
A stereoselective synthesis of the complete C1-C16 framework of tianchimycins A and B is described. Key transformations include Horner-Wadsworth-Emmons, Evans aldol, Gilman's and stereoselective alkylation reactions.
Jatrophane diterpenes: Preparation of the western fragment of pl-3
Lentsch, Christoph,Fuerst, Rita,Mulzer, Johann,Rinner, Uwe
, p. 919 - 923 (2014/03/21)
Jatrophane diterpenes are structurally intriguing natural products with promising biological properties. Herein, the synthesis of the western fragment of the Euphorbiaceae constituent Pl-3 starting from (1R,5S)-bicyclo[3.2.0]hept- 2-en-6-one is described. Key steps in the sequence include a Baeyer-Villiger oxidation, an iodolactonization reaction, and the installation of the northern side chain through the addition of a lithiated vinyl bromide. The overall efficiency of the route is increased by taking advantage of latent symmetry. The synthesis of the western fragment of Pl-3 is developed by taking advantage of the latent symmetry in an intermediate; both enantiomers are thus converted into the desired substrate. Key steps of the synthesis include a Baeyer-Villiger oxidation, an iodolactonization reaction, and the addition of a vinyllithium species to the completed cyclopentane moiety of the natural product.
