40360-71-2Relevant articles and documents
Total synthesis of anhydrolycorinone utilizing sequential intramolecular Diels-Alder reactions of a 1,3,4-oxadiazole
Wolkenberg, Scott E.,Boger, Dale L.
, p. 7361 - 7364 (2002)
A convergent total synthesis of anhydrolycorinone is detailed, enlisting sequential intramolecular Diels-Alder reactions of a suitably substituted 2-amino-1,3,4-oxadiazole defining a novel oxadiazole → furan → benzene Diels-Alder strategy.
Total synthesis of Amaryllidaceae alkaloids utilizing sequential intramolecular heterocyclic azadiene Diels-Alder reactions of an unsymmetrical 1,2,4,5-tetrazine
Boger,Wolkenberg
, p. 9120 - 9124 (2000)
Convergent total syntheses of anhydrolycorinone, hippadine, and anhydrolycorinium chloride are detailed, enlisting sequential inverse electron demand Diels-Alder reactions of an unsymmetrical N-acyl-6-amino-1,2,4,5-tetrazine.
Electrochemical Total Synthesis of Pyrrolophenanthridone Alkaloids: Controlling the Anodically Initiated Electron Transfer Process
Chiba, Kazuhiro,Okamoto, Kazuhiro
, p. 3613 - 3617 (2020/04/30)
Electrochemical intramolecular C(sp2)-H cross-coupling and dehydrogenative indole synthesis were developed. Both reactions were initiated by anodic oxidation of the same electron-rich indoline moiety, but the product selectivity was controlled
Schmidt Reaction of ω-Azido Valeryl Chlorides Followed by Intermolecular Trapping of the Rearrangement Ions: Synthesis of Assoanine and Related Pyrrolophenanthridine Alkaloids
DIng, Shao-Lei,Ji, Yang,Su, Yan,Li, Rui,Gu, Peiming
, p. 2012 - 2021 (2019/02/14)
The Schmidt reaction of ω-azido valeryl chlorides in the presence of an additional nucleophile was explored. The arenes, alcohols, and amines were demonstrated as the intermolecular trapping reagents for isocyanate ion and N-acyliminium ion from the Schmidt rearrangement, affording the corresponding products with moderate to excellent yields. Two 2-oxoindoles from the reaction were successfully converted into four natural alkaloids, namely, assoanine, anhydrolycorine, oxoassoanine, and anhydrolycorinone.
A Pd-catalyzed, boron ester-mediated, reductive cross-coupling of two aryl halides to synthesize tricyclic biaryls
Chen, Zhilong,Wang, Xiaodong
supporting information, p. 5790 - 5796 (2017/07/22)
Tricyclic biaryls are important scaffold structures in many natural products and lead compounds in drug discovery. The formation of a biaryl unit is often the key step for the synthesis of tricyclic biaryls. Despite significant progress toward the synthesis of biaryl compounds in recent years, the direct cross-coupling of two different aryl halides is still challenging and robust methods are lacking. Herein we report a direct cross-coupling of two different aryl halides in the presence of a palladium catalyst and boron ester, which provides a new and useful complementary method to synthesize tricyclic biaryls.
Construction of pyrrolophenanthridinone scaffolds mediated by samarium(II) diiodide and access to natural product synthesis
Suzuki, Kenji,Iwasaki, Hiroki,Domasu, Reika,Hitotsuyanagi, Naho,Wakizaka, Yuka,Tominaga, Mao,Kojima, Naoto,Ozeki, Minoru,Yamashita, Masayuki
, p. 5513 - 5519 (2015/08/03)
Pyrrolophenanthridinone derivatives including the natural products were readily synthesized by samarium(II)-mediated reductive cyclization of aryl radical onto a benzene ring under mild reaction conditions. This methodology was applied to the concise synt
Expeditious approach to pyrrolophenanthridones, phenanthridines, and benzo[ c ]phenanthridines via organocatalytic direct biaryl-coupling promoted by potassium tert -butoxide
De, Subhadip,Mishra, Sourabh,Kakde, Badrinath N.,Dey, Dhananjay,Bisai, Alakesh
, p. 7823 - 7844 (2013/09/12)
A methodology involving a "transition metal-free" intramolecular biaryl-coupling of o-halo-N-arylbenzylamines has been developed in the presence of potassium tert-butoxide and an organic molecule as catalyst. The reaction appears to proceed through KOtBu-promoted intramolecular homolytic aromatic substitution (HAS). Interestingly, this biaryl coupling also works in the presence of potassium tert-butoxide as sole promoter. On extending our approach further, we found that N-acyl 2-bromo-N-arylbenzylamines undergo a one-pot N-deprotection/biaryl coupling followed by oxidation, thus offering an expeditious route to the phenanthridine and benzo[c]phenanthridine skeletons. The strategy has been applied to a concise synthesis of Amaryllidaceae alkaloids viz. oxoassoanine (1b), anhydrolycorinone (1d), 5,6-dihydrobicolorine (2d), trispheridine (2b), and benzo[c]phenanthridines alkaloids dihydronitidine (3b), dihydrochelerythidine (3d), dihydroavicine (3f), nornitidine (3h), and norchelerythrine (3j).
Intramolecular direct dehydrohalide coupling promoted by KOtBu: Total synthesis of amaryllidaceae alkaloids anhydrolycorinone and oxoassoanine
De, Subhadip,Ghosh, Santanu,Bhunia, Subhajit,Sheikh, Javeed Ahmad,Bisai, Alakesh
supporting information, p. 4466 - 4469 (2012/10/29)
A transition-metal-free intramolecular dehydrohalide coupling via intramolecular homolytic aromatic substitution (HAS) with aryl radicals has been developed in the presence of potassium tert-butoxide and an organic molecule as the catalyst. The methodology has been applied to a concise synthesis of Amaryllidaceae alkaloids viz. oxoassoanine (1b), anhydrolycorinone (1d), and other related structures. Interestingly, the method also works only in the presence of potassium tert-butoxide.
In search of a cytostatic agent derived from the alkaloid lycorine: Synthesis and growth inhibitory properties of lycorine derivatives
Evdokimov, Nikolai M.,Lamoral-Theys, Delphine,Mathieu, Véronique,Andolfi, Anna,Frolova, Liliya V.,Pelly, Stephen C.,Van Otterlo, Willem A.L.,Magedov, Igor V.,Kiss, Robert,Evidente, Antonio,Kornienko, Alexander
, p. 7252 - 7261 (2012/01/30)
As a continuation of our studies aimed at the development of a new cytostatic agent derived from an Amaryllidaceae alkaloid lycorine, we synthesized 32 analogues of this natural product. This set of synthetic analogues included compounds incorporating sel
Simple synthesis of amides and weinreb amides Using PPh3 or PolymerSupported PPh3 and Iodine
Kumar, Amit,Akula, Hari Kiran,Lakshman, Mahesh K.
experimental part, p. 2709 - 2715 (2010/08/05)
The combination of PPh3/I2 has been shown to be effective for the conversion of a range of carboxylic acids into secondary, tertiary, and Weinreb amides. Simplification of the procedure was possible with the use of polymer-supported PPh3/ I2. Weinreb amides produced with the use of polymer-supported PPh3 could be filtered through a short silica gel plug and used in further transformations. Thus, the use of polymer-supported PPh3 offers potential applicability to diversityoriented reactions. Formal total syntheses of apocynin and pratosine, as well as syntheses of anhydrolychorinone and hippadine, have been achieved through the use of this amide-forming method. An attempt has been made to gain insight into this reaction.
