N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

• Joseane A. Mendes,
• Paulo R. R. Costa,
• Miguel Yus,
• Francisco Foubelo and
• Camilla D. Buarque

Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86

• led to (−)-pelletierine (112) alkaloid. Yus and co-workers developed the synthesis of the piperidine alkaloids (+)-dihydropinidine (122a), (+)-isosolenopsin (122b), (+)-isosolenopsin A (122c) and (2R,6R)-6-methylpipecolic acid hydrochloride by oxidation of the aromatic ring of (2R,6R)-2-methyl-6

• piperidine alkaloids isolated from fire ants (Solenopsis) and display hemolytic, insecticide and antibiotic properties. A straightforward synthesis of these natural products from a common imine intermediate was reported by Medjahdi et

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

• Iwona E. Głowacka,
• Aleksandra Trocha,
• Andrzej E. Wróblewski and
• Dorota G. Piotrowska

Beilstein J. Org. Chem. 2019, 15, 1722–1757, doi:10.3762/bjoc.15.168

• to synthesize the natural (2S,3R,4R,5R)-184 the lactone 186b was subjected to Mitsunobu reaction followed by the ester reduction and the hydrogenolytic cleavage of the 1-phenylethyl group. Piperidines: A cis-disubstituted piperidine scaffold was identified in several piperidine alkaloids of diverse

• for the aziridine ring opening and the removal of the 1-phenylethyl group and also for the reduction of the intermediate cyclic imine which appeared stereospecific. Two other piperidine alkaloids, (+)-deoxocassine ((2S,3S,6R)-190a) and (+)-spectaline ((2S,3S,6R)-190b) were synthesized as hydrochloride

Exploring architectures displaying multimeric presentations of a trihydroxypiperidine iminosugar

• Camilla Matassini,
• Stefania Mirabella,
• Andrea Goti,
• Inmaculada Robina,
• Antonio J. Moreno-Vargas and
• Francesca Cardona

Beilstein J. Org. Chem. 2015, 11, 2631–2640, doi:10.3762/bjoc.11.282

• glycosidases. Keywords: dendrimers; glycosidase inhibitors; iminosugars; multivalency; piperidine alkaloids; Introduction Iminosugars are well-known naturally occurring glycomimetics with a nitrogen atom replacing the endocyclic oxygen, mainly recognized as inhibitors of carbohydrate-processing enzymes

Recent applications of ring-rearrangement metathesis in organic synthesis

• Sambasivarao Kotha,
• Milind Meshram,
• Priti Khedkar,
• Shaibal Banerjee and
• Deepak Deodhar

Beilstein J. Org. Chem. 2015, 11, 1833–1864, doi:10.3762/bjoc.11.199

• this method by isolating the RCM product of the ROM–CM byproduct 290, which was recovered in the ROM–RCM–CM cascade (Scheme 62). Kouklovsky and co-workers [62] have described a stereoselective synthesis of 2-(2-hydroxyalkyl)piperidine alkaloids by employing a RRM of NDA adduct 293. The required

A new approach toward the total synthesis of (+)-batzellaside B

• Jolanta Wierzejska,
• Shin-ichi Motogoe,
• Yuto Makino,
• Tetsuya Sengoku,
• Masaki Takahashi and
• Hidemi Yoda

Beilstein J. Org. Chem. 2012, 8, 1831–1838, doi:10.3762/bjoc.8.210

• class of biologically potent piperidine alkaloids and related analogues. Examples of naturally occurring iminosugars. The chemical structures of (+)-batzellasides A–C (1a–c). Our previous approach to (+)-batzellaside B and retrosynthetic analysis for the new synthetic strategy. Reagents and conditions

Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles

• Pavol Jakubec,
• Dane M. Cockfield,
• Madeleine Helliwell,
• James Raftery and
• Darren J. Dixon

Beilstein J. Org. Chem. 2012, 8, 567–578, doi:10.3762/bjoc.8.64

• substituted piperidines. Keywords: cascade; imine; Michael addition; nitro-Mannich; organocatalysis; piperidine alkaloids; Introduction The piperidine ring is a common motif found in many biologically active natural products and drugs. The structures of these compounds range from the architecturally complex

Pd-catalysed [3 + 3] annelations in the stereoselective synthesis of indolizidines

• Olivier Y. Provoost,
• Andrew J. Hazelwood and
• Joseph P. A. Harrity

Beilstein J. Org. Chem. 2007, 3, No. 8, doi:10.1186/1860-5397-3-8

• and have attracted considerable attention because of their varied biological activity (some examples are illustrated in Scheme 1) [1]. Recent studies in our labs have demonstrated that a range of piperidine alkaloids, [2][3][4][5][6] including quinolizidine based targets, [7][8] can be prepared