106731-75-3Relevant academic research and scientific papers
Synthesis method of eribulin intermediate
-
Paragraph 0024; 0026; 0027, (2020/04/06)
The invention discloses a synthesis method of an eribulin intermediate. The synthesis method comprises the following steps: (1) carrying out an alkene-forming reaction Julia Olefination on a compoundrepresented by formula X and a compound represented by f
Formal Total Synthesis of Amphidinolide e
Bosch, Lluís,Mola, Laura,Petit, Elena,Saladrigas, Mar,Esteban, Jorge,Costa, Anna M.,Vilarrasa, Jaume
, p. 11021 - 11034 (2017/10/27)
A formal total synthesis of the cytotoxic macrolide amphidinolide E is reported. The strategic steps are three Julia-Kocienski reactions (J-K), for the formation of the C5-C6, C9-C10, and C17-C18 double bonds, a Suzuki-Molander C21-C22 bond formation reaction, and a Kita-Trost macrolactonization. The "instability" of the two dienic systems and of the stereocenter at C2 (allylic methine, α to the carboxy group) and the protecting groups at C17-OH and C18-OH have posed difficult challenges. Each Julia-Kocienski olefination has been systematically optimized to provide the highest possible E/Z ratios.
Halocarbocyclization entry into the oxabicyclo[4.3.1]decyl exomethylene-δ-lactone cores of linearifolin and zaluzanin A: Exploiting combinatorial catalysis
Ginotra, Sandeep K.,Friest, Jacob A.,Berkowitz, David B.
supporting information; experimental part, p. 968 - 971 (2012/04/04)
A streamlined entry into the sesquiterpene lactone (SQL) cores of linearifolin and zaluzanin A is described. Stereochemistry is controlled through transformations uncovered by ISES (In Situ Enzymatic Screening). Absolute stereochemistry derives from kinet
Synthesis of the spiroacetal fragment of broussonetine H
Brimble, Margaret A.,Park, Jae H.,Taylor, Carol M.
, p. 5861 - 5868 (2007/10/03)
(2S,6S)-2-(3-Bromopropyl)-1,7-dioxaspiro[5.5]undecane 3 was prepared by the addition of the acetylide derived from (4S)-4-benzyloxy-7-tert-butyldiphenylsilyloxyhep-1-yne 8 to δ-valerolactone 6 followed by treatment with hydrogen and palladium on charcoal which effected hydrogenation of the alkyne, hydrogenolysis of the benzyl ether and subsequent spiroacetal formation. The (4S)-stereochemistry in acetylene 8 was established by addition of trimethylsilylacetylene 10 to (2S)-epoxide 9, which in turn is derived from L-glutamic acid 11.
Intramolecular reaction of a phenonium ion. Novel lactonization of 4-aryl-5-tosyloxypentanoates and 4-aryl-5-tosyloxyhexanoates concomitant with a phenyl rearrangement
Nagumo, Shinji,Ono, Machiko,Kakimoto, Yo-ichiro,Furukawa, Tsuneo,Hisano, Tomoaki,Mizukami, Megumi,Kawahara, Norio,Akita, Hiroyuki
, p. 6618 - 6622 (2007/10/03)
The novel lactonizations of methyl 4-aryl-5-tosyloxypentanoate 1 and 4-aryl-5-tosyloxyhexanoate 3 concomitant with a phenyl rearrangement are reported. The lactonizations were promoted by silica gel or heating in various solvents. By examining the effects of substituents of the aromatic ring on the reactivity, it was found that the reaction proceeded via a phenonium ion. This finding was supported by the stereochemical results for the lactonization of optical active 1. Silica gel-promoted lactonization of 1 gave only γ-lactone 2, whereas that of 3 afforded γ-lactone 4 and δ-lactone 5. These lactonizations proved to be kinetically controlled. On the other hand, when 3c was heated in CH3NO2 at 70°C, the highly selective formation of 4c was observed. Further detailed experiments confirmed that the thermal lactonization in CH3NO2 was thermodynamically controlled.
Total synthesis of calonyctin A2, a macrolidic glycolipid with plant growth-promoting activity
Furukawa, Jun-Ichi,Kobayashi, Shigeru,Nomizu, Motoyoshi,Nishi, Norio,Sakairi, Nobuo
, p. 3453 - 3457 (2007/10/03)
Calonyctin A2, a tetrasaccharidic glycolipid having a 22-membered macrolidic structure, has been synthesized by the assembly of three 6- deoxygenated thioglycoside intermediates. The short-step synthesis was achieved by preparation of the most complicated
Novel lactonization induced by the phenonium ion
Nagumo, Shinji,Furukawa, Tsuneo,Ono, Machiko,Akita, Hiroyuki
, p. 2849 - 2852 (2007/10/03)
Silica gel promotes the lactonization and the concomitant aryl rearrangement of 4-aryl-5-tosyloxy pentanoates (3c-j) to give γ-lactones along with complete inversion in high yields.
Diastereoselective synthesis of 2,5-disubstituted 3-hydroxypyrrolidine and 2,6-disubstituted 3-hydroxypiperidine derivatives by radical cyclisation; synthesis of (+)-bulgecinine and (-)-desoxoprosopinine
Yuasa, Yoko,Ando, Jun,Shibuya, Shiroshi
, p. 793 - 802 (2007/10/03)
Cyclisation of the O-stannyl ketyl, generated from the aldehyde 17 by reaction with tributyltin hydride in the presence of AIBN, gives the 5-benzyloxymethyl-7-hydroxypyrrolooxazolidin-2-ones as a diastereoisomeric mixture of 7α-ol 18 and 7β-ol 19 (2:1), with high diastereoselectivity with respect to the 5,7a positions. (+)-Bulgecinine 8 is enantioselectively synthesised by stereospecific reduction of the ketone 20, derived from compounds 18 and 19. In a similar way, cyclisation of compound 40 gives a 2:1 mixture of compounds 41 and 42. Conversion of compound 41 into (-)-desoxoprosopinine 9 is successfully achieved.
Enantioselective synthesis of (-)-desoxoprosopinine by radical cyclization
Yuasa,Ando,Shibuya
, p. 1525 - 1526 (2007/10/02)
Reaction of the aldehyde 12 with tributyrin hydride in the presence of AIBN gave a mixture of 13 as a 2:1 mixture of 8β-ol and 8α-ol. Conversion of 14, derived from 13, to (-)-desoxoprosopinine 3 was successfully achieved.
