16958-42-2Relevant academic research and scientific papers
Total Synthesis of Haliclonin A
Jin, Yuan,Orihara, Kensuke,Kawagishi, Fumiki,Toma, Tatsuya,Fukuyama, Tohru,Yokoshima, Satoshi
, p. 9666 - 9671 (2021)
The total synthesis of haliclonin A was accomplished. Starting from 3,5-dimethoxybenzoic acid, a functionalized cyclohexanone fused to a 17-membered ring was prepared through a Birch reduction/alkylation sequence, ring-closing metathesis, intramolecular cyclopropanation, and stereoselective 1,4-addition of an organocopper reagent to an enone moiety. Reductive C?N bond formation via an N,O-acetal forged the 3-azabicyclo[3.3.1]nonane core. The allyl alcohol moiety was constructed by a sequence involving stereoselective α-selenylation of an aldehyde via an enamine, syn-elimination of a selenoxide, and allylation of the aldehyde with an allylboronate. Formation of the 15-membered ring containing a skipped diene was achieved by ring-closing metathesis, and final transformations led to the synthesis of haliclonin A.
THERMOLYSE ET PHOTOLYSE DE CETONES NON SATUREES XXVII. SYNTHESE DE COMPOSES BICYCLIQUES PAR DOUBLE THERMOCYCLISATION DE DIENONES ET DE DIENEDIONES
Drouin, J.,Leyendecker, F.,Conia, J. M.
, p. 1195 - 1202 (1980)
The thermal isomerisation of some dienones and dienediones is explored as a route to bi- and polycyclic compounds.A dicyclopentylketone (6, from 3), two 3a-acetyl-cis-perhydropentalenes (32 and 33, from 29) and two spirononane-1,6 diones (27 and 28,
A Metathesis Route to (+)-Orientalol F, a Guaiane Sesquiterpene from Alisma Orientalis
Zahel, Martin,Wang, Yuzhou,J?ger, Anne,Metz, Peter
, p. 5881 - 5886 (2016)
The synthesis of (+)-orientalol F (1) started with aldehyde 6, which is available from (R)-limonene in two steps. Wittig reaction of 6 with unsaturated ylide 7 to give a tetraene, and subsequent ring-closing metathesis yielded hydroazulene 4, selective ep
Formal Synthesis of (-)-Haliclonin A: Stereoselective Construction of an Azabicyclo[3.3.1]nonane Ring System by a Tandem Radical Reaction
Komine, Keita,Urayama, Yasuhiro,Hosaka, Taku,Yamashita, Yuki,Fukuda, Hayato,Hatakeyama, Susumi,Ishihara, Jun
supporting information, p. 5046 - 5050 (2020/07/04)
A formal synthesis of (-)-haliclonin A, isolated from the marine sponge Haliclona sp. in Korea, is described. The key feature of the synthesis includes the highly stereoselective tandem radical reaction to construct the azabicyclo[3.3.1]nonane core and the enantioselective formation of an all-carbon quaternary center via the Pd-mediated deracemization.
Evolution of an oxidative dearomatization enabled total synthesis of vinigrol
Yang, Qingliang,Draghici, Cristian,Njardarson, Jon T.,Li, Fang,Smith, Brandon R.,Das, Pradipta
supporting information, p. 330 - 344 (2014/01/06)
The evolution of the synthetic strategy resulting in a total synthesis of vinigrol is presented. Oxidative dearomatization/intramolecular Diels-Alder cycloaddition has served as the successful cornerstone for all of the approaches. Extensive radical cyclization efforts to form the tetracyclic core resulted in interesting and surprising reaction outcomes, none of which could be advanced to vinigrol. These cyclization obstacles were successfully overcome by using Heck instead of radical cyclizations. The total synthesis features a trifluoroethyl ether protecting group being used for the first time in organic synthesis. The logic of its selection and the group's importance beyond protecting the C8a hydroxyl group is presented along with a discussion of strategies for its removal. Because of the compact tetracyclic cage the route is built around many unusual reaction observations and solutions have emerged. For example, a first of its kind Grob fragmentation reaction featuring a trifluoroethyl leaving group has been uncovered, interesting interrupted selenium dioxide allylic oxidations have been observed as well as intriguing catalyst and counterion dependent directed hydrogenations.
A biosynthetically-inspired synthesis of the tetrahydrofuran core of obtusallenes II and IV
Braddock, D. Christopher,Bhuva, Roshni,Millan, David S.,Perez-Fuertes, Yolanda,Roberts, Craig A.,Sheppard, Richard N.,Solanki, Savade,Stokes, Elaine S. E.,White, Andrew J. P.
, p. 445 - 448 (2007/10/03)
Sharpless asymmetric dihydroxylation was regioselective for the frans olefin in an E vs Z vs terminal triene substrate. To test a biosynthetic hypothesis, the resulting diol underwent diastereoselective bromoetherification to provide the des-chloro core o
Synthesis of 2-amino-octa-4,7-dien-1-ol (2): Key intermediate for mycothiazole natural product and analogs
Mahler, Graciela,Serra, Gloria,Manta, Eduardo
, p. 1481 - 1492 (2007/10/03)
Starting from L-aminoacids, facile methods for the preparation 2-aminocta-4,7-dien-ol with different stereochemistry have been developed as key intermediates of mycothiazole and analogs. Copyright Taylor & Francis, Inc.
Halomethyl derivatives of gamma-aminobutyric acid and related compounds
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, (2008/06/13)
Novel compounds of the following general formula are useful pharmacological agents: STR1 wherein Y is FCH2 - or F2 CH-; R1 is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, -NR10 R11 wherein each of R10 and R11 is hydrogen or a straight or branched alkyl group of from 1 to 4 carbon atoms or STR2 wherein R12 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R2 is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched or STR3 wherein R8 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; and n is the integer 2 or 3; pharmaceutically acceptable salts and individual optical isomers thereof.
