852834-02-7Relevant academic research and scientific papers
Formal Total Synthesis of Actinoranone: Synthesis Approaches and Cytotoxic Studies
Novaes, Luiz F. T.,Gon?alves, Kaliandra De Almeida,Trivella, Daniela B. B.,Pastre, Julio C.
, p. 5160 - 5176 (2018/05/17)
This article describes our efforts toward the total synthesis of actinoranone. Our synthesis strategies rely on a convergent route to connect the terpenoid and polyketide fragments, employing catalysis and powerful classical reactions for the assembly of
Synthesis of axially chiral C10-BridgePHOS oxides and their use as organocatalysts in enantioselective allylations of aldehydes
Chen, Jianzhong,Liu, Delong,Fan, Dongyang,Liu, Yangang,Zhang, Wanbin
, p. 8161 - 8168 (2013/09/02)
A series of C10-BridgePHOS oxides possessing different substituted groups on the diphenyl phosphine system were synthesized and tested as organocatalysts in the allylation of aldehydes with allyltrichlorosilane, providing chiral homoallylic alc
Tetrahydroisoquinoline-based N-oxides as chiral organocatalysts for the asymmetric allylation of aldehydes
Naicker, Tricia,Arvidsson, Per I.,Kruger, Hendrik G.,Maguire, Glenn E. M.,Govender, Thavendran
experimental part, p. 6923 - 6932 (2012/01/06)
The short synthesis of a series of novel chiral N-oxideorganocatalysts and their evaluation in the asymmetric allylation reaction of aromatic and α-β-unsaturated aldehydes with allyltrichlorosilane is reported. These readily modifiable organocatalysts are
Development of chiral dinitrones as modular Lewis base catalysts: Asymmetric allylation of aldehydes with allyltrichlorosilanes
Seon Oh, Young,Kotani, Shunsuke,Sugiura, Masaharu,Nakajima, Makoto
experimental part, p. 1833 - 1835 (2010/11/05)
Chiral dinitrones were synthesized by the condensation of a C 2-symmetrical chiral dihydroxylamine with various aldehydes. The electronic and steric properties of the dinitrones can be modified by changing the aldehyde component. The activity o
Synthesis and assignment of the absolute configuration of the anti-Helicobacter pylori agents CJ-12,954 and CJ-13,014
Brimble, Margaret A.,Bryant, Christina J.
, p. 2858 - 2866 (2008/03/12)
The synthesis of the spiroacetal-containing anti-Helicobacter pylori agents (3S,2″S,5″S,7″S)-1a (ent-CJ-12,954) and (3S,2″S, 5″R,7″S)-2a (ent-CJ-13,014) has been carried out based on the convergent union of a 1: 1 mixture of heterocycle-activated spiroace
A cyclopropanol-based strategy for subunit coupling: Total synthesis of (+)-spirolaxine methyl ether
Keaton, Katie A.,Phillips, Andrew J.
, p. 2717 - 2719 (2008/02/09)
Equation Presented A strategy for ketone synthesis with cyclopropanols as intermediates and its application to (+)-spirolaxine methyl ether is described. The synthesis also features an application of Fu's alkyl-alkyl Suzuki coupling.
Synthesis of the anti-Helicobacter pylori agent (+)-spirolaxine methyl ether and the unnatural (2″S)-diastereomer
Robinson, James E.,Brimble, Margaret A.
, p. 2572 - 2582 (2008/03/12)
The first enantioselective synthesis of the anti-Heliocbacter pylori agent (+)-spirolaxine methyl ether 2b has been carried out in a convergent fashion establishing that the absolute stereochemistry of the natural product is in fact (3R, 2″R, 5″R, 7″R) after initial synthesis of the unnatural (2″S)-diastereomer 2a. The key step in the synthesis of (+)-spirolaxine methyl ether 2b involved a heterocycle-activated Julia-Kocienski olefination between benzothiazole-based spiroacetal sulfone 4b and phthalide aldehyde 3a. (2″R, 5″S, 7″S)-Spiroacetal sulfone 4b was prepared via cyclisation of protected dihydroxyketone 6b, which in turn was derived from the coupling of the acetylide derived from (R)-acetylene 24b with aldehyde 3a. Phthalide aldehyde 3a was prepared via intramolecular acylation of bromocarbamate 15, which was available via titanium tetrafluoride-(+)-BINOL- mediated allylation of 3,5-dimethoxybenzaldehyde 13. Union of the sulfone 4b and aldehyde 3a fragments successfully completed the enantioselective synthesis of (+)-spirolaxine methyl ether 2b. The synthesis of the unnatural (3R, 2″S, 5″R, 7″R)-diastereomer of spirolaxine methyl ether 2a was also undertaken in a similar manner by union of phthalide aldehyde 3a with (2″S, 5″S, 7″S)-spiroacetal sulfone 4a derived from (S)-acetylene 24a. The Royal Society of Chemistry.
Synthesis of the spiroacetal-containing anti-Helicobacter pylori agents CJ-12,954 and CJ-13,014
Brimble, Margaret A.,Bryant, Christina J.
, p. 4506 - 4508 (2008/09/18)
The first synthesis of the spiroacetal-containing anti-Helicobacter pylori agents ent-CJ-12,954 and ent-CJ-13,014 is reported based on the union of a heterocycle-activated spiroacetal-containing sulfone fragment with a phthalide-containing aldehyde fragme
The first enantioselective total synthesis of the anti-Helicobacter pylori agent (+)-spirolaxine methyl ether
Robinson, James E.,Brimble, Margaret A.
, p. 1560 - 1562 (2007/10/03)
The first enantioselective synthesis of the anti-Helicobacter pylori agent (+)-spirolaxine methyl ether has been carried out in a convergent fashion by heterocycle-activated Julia olefination of a spiroacetal-containing sulfone fragment with a phthalide-containing aldehyde fragment. The total synthesis of (+)-spirolaxine methyl ether establishes the absolute stereochemistry of the natural product to be (3R,2″R,5″R,7″R). The Royal Society of Chemistry 2005.
