446264-36-4Relevant academic research and scientific papers
Total synthesis of maoecrystal V: Early-stage C-H functionalization and lactone assembly by radical cyclization
Lu, Ping,Gu, Zhenhua,Zakarian, Armen
, p. 14552 - 14555 (2013)
A total synthesis of the unusual ent-kaurane maoecrystal V is described. The synthesis strategy features a counterintuitive early disconnection of the lactone subunit to a polycyclic enol ether intermediate in order to preserve the central tetrahydrofuran ring until the beginning stages of the synthesis. This strategy enables an application of C-H functionalization at the early phase of the synthesis during the construction of a dihydrobenzofuran intermediate.
4-ALKYNYL IMIDAZOLE DERIVATIVE AND MEDICINE COMPRISING SAME AS ACTIVE INGREDIENT
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Paragraph 0275, (2016/06/06)
There are provided 4-alkynylimidazole derivatives represented by the following general formula (I) or phamaceutically acceptable salts thereof; the derivatives have a superior EP4 receptor antagonistic action and are useful as pharmaceuticals for the trea
4-ALKYNYL IMIDAZOLE DERIVATIVE AND MEDICINE COMPRISING SAME AS ACTIVE INGREDIENT
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Paragraph 0424; 0425, (2016/10/10)
There are provided 4-alkynylimidazole derivatives represented by the following general formula (I) or phamaceutically acceptable salts thereof; the derivatives have a superior EP4 receptor antagonistic action and are useful as pharmaceuticals for the trea
Enantioselective synthesis of (-)-maoecrystal v by enantiodetermining C-H functionalization
Lu, Ping,Mailyan, Artur,Gu, Zhenhua,Guptill, David M.,Wang, Hengbin,Davies, Huw M. L.,Zakarian, Armen
supporting information, p. 17738 - 17749 (2015/02/19)
The evolution of a program directed at the enantioselective total synthesis of maoecrystal V, a highly modified ent-kauranoid, is described. An early stage chiral auxiliary-directed asymmetric C-H functionalization for the construction of a key benzofuran intermediate enabled the first asymmetric synthesis of the natural enantiomer of maoecrystal V, confirming the assigned stereochemistry. A divergent course of the central intramolecular Diels-Alder reaction, which is dependent on the nature of the dienophile, initially led to the development of an unanticipated and previously unknown isomer of maoecrystal V, which we named maoecrystal ZG. In light of the reported selective and potent cytotoxic activity of maoecrystal V, the cytotoxic properties of maoecrystal ZG were also investigated.
Stereoselective synthesis of 1,3-anti diols by an Ipc-mediated domino aldol-coupling/reduction sequence
Dieckmann, Michael,Menche, Dirk
supporting information, p. 228 - 231 (2013/03/28)
A novel domino process for 1,3-anti diol synthesis by the union of a methyl ketone with an aldehyde is described. The operationally simple procedure is based on an Ipc-boron-aldol coupling and subsequent Ipc-mediated reduction of the intermediate β-hydrox
Modular total synthesis of rhizopodin: A highly potent G-actin dimerizing macrolide
Kretschmer, Manuel,Dieckmann, Michael,Li, Pengfei,Rudolph, Sven,Herkommer, Daniel,Troendlin, Johannes,Menche, Dirk
supporting information, p. 15993 - 16018 (2014/04/03)
A highly convergent total synthesis of the potent polyketide macrolide rhizopodin has been achieved in 29steps by employing a concise strategy that exploits the molecule′s C2 symmetry. Notable features of this convergent approach include a rapid assembly of the macrocycle through a site-directed sequential cross-coupling strategy and the bidirectional attachment of the side chains by means of Horner-Wadsworth-Emmons (HWE) coupling reactions. During the course of this endeavor, scalable routes for synthesis of three main building blocks of similar complexity were developed that allowed for their stereocontrolled construction. This modular route will be amenable to the development of syntheses of other analogues of rhizopodin.
Distinct chemoselectivities in the platinum-catalyzed 1,2- carboalkoxylations of 5-alkoxypent-1-yn-3-ol derivatives
Ting, Chun-Ming,Wang, Chiou-Dong,Chaudhuri, Rupsha,Liu, Rai-Shung
supporting information; experimental part, p. 1702 - 1705 (2011/06/17)
Two distinct Pt-catalyzed carboalkoxylations of alkynes are reported. The cycloisomerization of 5-alkoxypent-1-yn-3-ol derivatives 5 produces 2,6-dioxabicyclo[3.1.0]hexanes 6; the mechanism is postulated to involve a hydroxyl-triggered [3.3]-sigmatropic a
Elongation of 1,3-polyols via iterative catalyst-directed carbonyl allylation from the alcohol oxidation level
Hassan, Abbas,Lu, Yu,Krische, Michael J.
supporting information; experimental part, p. 3112 - 3115 (2009/12/05)
Iterative enantioselective carbonyl allylation from the alcohol oxidation level under the conditions of iridium catalyzed transfer hydrogenation enables chain elongation of 1,3-polyols. High levels of catalyst-directed enantioselectivity and diastereosele
Toward the synthesis of peloruside A: Fragment synthesis and coupling studies
Paterson, Ian,Di Francesco, M. Emilia,Kuehn, Toralf
, p. 599 - 602 (2007/10/03)
(Matrix presented). The asymmetric synthesis of building blocks 3, 4, and 5, corresponding to C12-C19, C7-C 11, and C1-C6 segments of peloruside A, is reported, along with boron-mediated al
Conformational analysis of oligo-1,3-dioxanylmethanes
Trieselmann, Thomas,Hoffmann, Reinhard W.,Menzel, Karsten
, p. 1292 - 1304 (2007/10/03)
Stereoselective synthesis of a series of 1,3-dioxan-4-ylmethanes 1-9 has been achieved by use of solely substrate-based asymmetric induction. The simple C2-symmetric bis(dioxanyl)methane 1 has a greater than 99% conformational preference at the two inter-ring bonds for the conformation 1a. The homologous structures 3-9 contain up to five dioxanylmethane units, maintaining a high conformational preference in each of the bis(dioxanyl)methane units. Thus, these flexible compounds reach a conformational preference in excess of 90% over up to eight rotatable interring bonds. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
