67217-85-0Relevant academic research and scientific papers
Cross-coupling of cyclopropanols: Concise syntheses of indolizidine 223AB and congeners
Rao, Nagavaram Narsimha,Parida, Bibhuti Bhusan,Cha, Jin Kun
, p. 6208 - 6211 (2014)
A new synthetic method for indolizidine or pyrrolizidine alkaloids based on readily available and attractively functionalized cyclopropanols, as exemplified in concise syntheses of indolizidine (-)-223AB, its 3-epimer, (-)-indolizidine 239AB, and (-)-indolizidine 239CD, is reported. This work highlights the applications of SN2′ alkylation and C-acylation of cyclopropanols to meet stereochemical challenges in natural product synthesis. Also included is diastereoselective cyclization of the resulting aminoallene adduct for bicyclic ring formation.
C-H Functionalization of Amino Alcohols by Osmium Tetroxide/NMO or TPAP/NMO: Protecting Group-Free Synthesis of Indolizidines (–)-223AB and 3-epi-(–)-223AB
Chen, Wei-Lun,Wang, Lee-Ya,Li, Yu-Jang
, p. 103 - 107 (2020/01/02)
The oxidative cyclization of amino alcohols by osmium tetroxide/NMO or tetrapropylammonium perruthenate (TPAP)/NMO was found to provide an N,O-acetal moiety through the trapping of the resulting iminium ion by the alcohol. These two transformations were demonstrated in the synthesis of indolizidines (–)-223AB and 3-epi-(–)-223AB.
Enantiopure 2,6-disubstituted piperidines bearing one alkene- or alkyne-containing substituent: Preparation and application to total syntheses of indolizidine-alkaloids
Liu, Hui,Su, Deyong,Cheng, Guolin,Xu, Jimin,Wang, Xinyan,Hu, Yuefei
supporting information; experimental part, p. 1899 - 1904 (2010/08/21)
A general and efficient procedure for the preparation of 2,6-disubstituted piperidines bearing one alkene- or alkyne-containing substituent was developed by using non-racemic Betti base as a chiral auxiliary. Many chiral benzylamines are excellent auxiliaries, but they were rarely used for this purpose because of the inefficient removal of the N-benzyl auxiliary residue under non-hydrogenative conditions. We found that N,N-disubstituted Betti base derivative has a typical Mannich structure of o-naphthol. When it carried out a base-catalyzed formation of o-quinone methide, an efficient non-hydrogenative N-debenzylation was achieved, and the alkene and alkyne groups survived. To demonstrate the efficiency of the method and the versatility of the products, asymmetric total syntheses of indolizidine-alkaloids (-)-167B, (-)-195H, (-)-209D and (-)-223AB were accomplished.
Asymmetric synthesis of 3,5-disubstituted indolizidines by intermolecular addition of an allylsilane on an N-acyliminium ion
Conchon, Elisabeth,Gelas-Mialhe, Yvonne,Remuson, Roland
, p. 1253 - 1257 (2007/10/03)
A diastereoselective synthesis of 3,5-disubstituted indolizidines based on an intermolecular addition of an allylsilane on an acyliminium ion derived from (S)-pyroglutamic acid is described. The synthetic potential of this methodology is demonstrated by t
A general, convergent strategy for the construction of indolizidine alkaloids: Total syntheses of (-)-indolizidine 223AB and alkaloid (-)-205B
Smith III, Amos B.,Kim, Dae-Shik
, p. 2547 - 2557 (2007/10/03)
N-Toluenesulfonyl aziridines comprise effective second electrophiles in the solvent controlled three-component linchpin union of silyl dithianes for the stereocontrolled convergent elaboration of protected 1,5-amino alcohols. This tactic, in conjunction w
Multicomponent linchpin coupling of silyl dithianes employing an N-Ts aziridine as the second electrophile: Synthesis of (-)-indolizidine 223AB
Smith III, Amos B.,Kim, Dae-Shik
, p. 1493 - 1495 (2007/10/03)
An efficient, stereocontrolled assembly of the indolizidine alkaloid, (-)-indolizidine 223AB, exploiting a three-component linchpin coupling employing an N-Ts aziridine as the second electrophile, followed by a one-pot sequential construction of the indol
Radical cyclization of beta-aminoacrylates: synthesis of (-)-indolizidine 223AB.
Lee,Jeong,Min,Hong,Lim,Kim,Kim,Choi,Koo
, p. 2169 - 2171 (2007/10/03)
[reaction: see text] (-)-Indolizidine 223AB was synthesized via radical cyclization of the beta-aminoacrylate derivative of a trans-2,5-disubstituted pyrrolidine. The trans-2,5-disubstituted pyrrolidine substrate was prepared by radical cyclization of a S
Synthesis of indolizidines (-)-195B, (-)-223AB and (-)-239AB: (2S,5R)- l-[(benzyloxy)carbonyl]-2-methoxycarbonyl-5-(4pentenyl)pyrrolidine as a versatile chiral building block
Celimene, Catherine,Dhimane, Hamid,Lhommet, Gerard
, p. 10457 - 10468 (2007/10/03)
The total syntheses of three levogyre 3,5-disubstituted indolizidines, (-)-195B, (-)-223AB and (-)-239AB are described. The employed strategy is based on the utilization of the common enantiopure trans 2,5-disubstituted pyrrolidine 3, which is assembled b
Bicyclo[3.3.1]nonanes as synthetic intermediates. Part 20. Asymmetric synthesis of the indolizidine alkaloids monomorine I and indolizidine 223AB
Momose, Takefumi,Toshima, Minoru,Seki, Sumie,Koike, Yayoi,Toyooka, Naoki,Hirai, Yoshiro
, p. 1315 - 1321 (2007/10/03)
Total syntheses of the indolizidine alkaloids monomorine I and indolizidine 223AB have been achieved by starting from the chiral cis-2,5-disubstituted pyrrolidine or cis-2,6-disubstituted piperidine obtained from the asymmetric cleavage of 8-azabicyclo[3.2.1]octan-3-one or 9-azabicyclo[3.3.1]nonan-3-one at the 'fork head'.
One-pot preparation of quinolizidin-2-one and indolizidin-7-one ring systems. Concise total synthesis of (±)-myrtine, (±)-lasubine II, and (-)-indolizidine 223AB
Pilli,Carlos Dias,Maldaner
, p. 717 - 722 (2007/10/02)
A highly efficient approach to the quinolizidine alkaloids (±)-myrtine (4) and (±)-lasubine II (5) and to the indolizidine alkaloid (-)-indolizidine 223AB (6) is described. The preparation of quinolizidin-2-ones 4/4a and 11b/12b and indolizidin-7-ones 16/
