214914-86-0Relevant academic research and scientific papers
Total synthesis of four stereoisomers of (5Z,8Z,10E,14Z)-12-hydroxy-17,18-epoxy-5,8,10,14-eicosatetraenoic acid and their anti-inflammatory activities
Goto, Tomomi,Urabe, Daisuke,Isobe, Yosuke,Arita, Makoto,Inoue, Masayuki
, p. 8320 - 8332 (2015/10/05)
The four stereoisomers of novel lipid mediator 1, (5Z,8Z,10E,14Z)-12-hydroxy-17,18-epoxy-5,8,10,14-eicosatetraenoic acid, were synthesized from six simple fragments. Triyne 2 was convergently assembled through three SN2 alkynylation reactions a
Total synthesis of (-)-goniotrionin
Dias, Luiz C.,Ferreira, Marco A. B.
experimental part, p. 4046 - 4062 (2012/06/29)
A stereoselective total synthesis of the reported structure of goniotrionin (4) has been accomplished. The key steps involved the opening of a chiral epoxide, a highly diastereoselective Mukaiyama aerobic oxidative cyclization, a selective 1,2-syn Mukaiyama aldol reaction, and a Noyori reduction.
A convergent synthesis of the C31-C46 fragment of phorboxazoles
Yadav,Rajaiah
, p. 1743 - 1746 (2007/10/03)
A convergent synthesis of the C31-C46 fragment of phorboxazoles has been achieved. This involved the preparation of a C31-C39 aldehyde and a C40-C46 benzothiazole secondary sulfone followed by their coupling, employing modified Julia olefination as a key
A convergent synthesis of the C31-C46 fragment of phorboxazoles
Yadav,Rajaiah
, p. 1537 - 1540 (2007/10/03)
A convergent synthesis of the C31-C46 fragment of phorboxazoles has been achieved. This involved the preparation of a C31-C39 aldehyde and a C40-C46 benzothiazole secondary sulphone followed by their coupling, employing modified Julia olefination as a key
An approach to the C(10)-C(16) fragment of the bryostatins: Stereoselective exocyclic double-bond formation by vinyl radical cyclization
Maguire, Robert J.,Munt, Simon P.,Thomas, Eric J.
, p. 2853 - 2863 (2007/10/03)
On treatment with tributyltin hydride, the vinyl bromide 11 and the vinyl iodide 26 cyclize to give mixtures of the (E)- and (Z)-4-(alkoxycarbonylmethylene)tetrahydropyrans 12/13 and 27/28 in which the (E)-isomers 12 and 27 are the major components accounting for 80% of the products. Addition of triphenyltin hydride to the alkyne 34 similarly initiates cyclization giving a mixture of products 35-37, the composition of the mixture depending upon the concentration of the tin hydride. These results are consistent with faster cyclization of the (Z)-vinyl radical with kinetic formation of five-membered ring containing products which are either trapped by hydrogen transfer from the tin hydride or which rearrange to form a 4-methylenetetrahydropyran. This chemistry was applied to prepare the cis-2,6-disubstituted 4-(methoxycarbonylmethylene)tetrahydropyran 50 which may be useful for the introduction of the C(10)-C(16) fragment into the bryostatins. Cyclization of the p-methoxybenzyl protected vinyl iodide 58 is less stereoselective, perhaps because of intramolecular hydrogen transfer from the p-methoxybenzyl group.
