4.8 Article

Total Synthesis of Pyrrolidine and Piperidine Natural Products via TMSOTf-Mediated 5/6-endo-dig Reductive Hydroamination of Enynyl Amines

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Article Chemistry, Organic

Lewis-Acid-Catalyzed Reductive Hydroalkoxylation of Propargylic N-Hydroxylamines Gives Stereoselective Access to Isoxazolidines

Santosh J. Gharpure et al.

Summary: A new method was developed for the stereoselective synthesis of isoxazolidine derivatives via Lewis acid-catalyzed 5-endo-dig reductive hydroalkoxylation cascade on propargylic N-hydroxylamine. This method provides an efficient approach to biologically active isoxazolidine scaffolds. The synthetic potential of this methodology was demonstrated by synthesizing 1,3-aminoalcohol, 4-aminotetrahydropyran, and sedamine natural products.

ORGANIC LETTERS (2023)

Article Chemistry, Organic

Collective Asymmetric Total Synthesis of Cylindricines

Ryohei Hanzawa et al.

Summary: A collective asymmetric total synthesis of marine tricyclic alkaloids, cylindricines A-H, as well as the proposed structures of cylindricines I and J, was accomplished from a single common spirocyclic pyrrolidine intermediate in a concise manner. A tandem chemoselective oxidation/intramolecular aza-Michael addition/epimerization strategy was utilized to successfully construct the tricyclic skeleton. This work presents a versatile synthetic approach to the cylindricine family of marine tricyclic alkaloids.

ORGANIC LETTERS (2023)

Article Chemistry, Organic

Lewis-Acid-Catalyzed Reductive Hydroalkoxylation of Propargylic N-Hydroxylamines Gives Stereoselective Access to Isoxazolidines

Santosh J. Gharpure et al.

Summary: Lewis acid-catalyzed 5-endo-dig reductive hydro-alkoxylation cascade on propargylic N-hydroxylamine enables efficient and stereoselective synthesis of isoxazolidine derivatives, which are biologically privileged scaffolds. The synthetic potential of this method is demonstrated by the synthesis of 1,3-aminoalcohol, 4-aminotetrahydropyran, and sed-amine natural products.

ORGANIC LETTERS (2023)

Article Chemistry, Organic

Stereoselective Tandem Synthesis of Pyrrolidine Derivatives under Gold Catalysis: An Asymmetric Synthesis of (-)-Lepadiformine A

Atsushi Yoshimura et al.

Summary: An Au-catalyzed tandem reaction was developed for the efficient synthesis of pyrrolidine derivatives with a tetrasubstituted carbon stereocenter. The reaction was successfully applied to the asymmetric synthesis of (-)-lepadiformine A, a marine cytotoxic tricyclic alkaloid.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Pyrrolidine and Indolizidine Alkaloids from Chiral N-tert-Butanesulfinyl Imines Derived from 4-Halobutanal

Ana Sirvent et al.

Summary: An efficient stereocontrolled preparation of 2-substituted pyrrolidines and 5-substituted indolizidin-7-ones using chiral N-tert-butanesulfinyl imines derived from 4-halobutanal as starting materials. The high diastereoselectivity in Grignard reagents addition and decarboxylative Mannich reaction with α-keto acids with these chiral imines is demonstrated for the synthesis of various pyrrolidinic alkaloids.

SYNTHESIS-STUTTGART (2021)

Review Chemistry, Multidisciplinary

Pyrrolidine in Drug Discovery: A Versatile Scaffold for Novel Biologically Active Compounds

Giovanna Li Petri et al.

Summary: The five-membered pyrrolidine ring and its derivatives have demonstrated bioactivity with target selectivity for treating human diseases. By comparing the physicochemical parameters of pyrrolidine with the parent aromatic pyrrole and cyclopentane, the influence of steric factors on biological activity was investigated, along with describing the structure-activity relationship of the studied compounds.

TOPICS IN CURRENT CHEMISTRY (2021)

Review Pharmacology & Pharmacy

Pyrrolidine alkaloids and their promises in pharmacotherapy

Muhammad Torequl Islam et al.

ADVANCES IN TRADITIONAL MEDICINE (2020)

Article Chemistry, Multidisciplinary

Mannich-type Reactions of Cyclic Nitrones: Effective Methods for the Enantioselective Synthesis of Piperidine-containing Alkaloids

Vladislav G. Lisnyak et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Medicinal

Rings in Drugs

Richard D. Taylor et al.

JOURNAL OF MEDICINAL CHEMISTRY (2014)

Article Chemistry, Organic

Synthesis of azimic acid using hydroformylation

Roderick W. Bates et al.

TETRAHEDRON (2013)

Article Chemistry, Organic

Stereocontrolled synthesis of piperidine alkaloids, (-)-241D and (-)-isosolenopsin

R. V. N. S. Murali et al.

TETRAHEDRON LETTERS (2012)

Article Chemistry, Inorganic & Nuclear

Alkyne hydroamination triggered cyclizations: A powerful tool for the construction of biologically important structural motifs

Nitin T. Patil et al.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2011)

Article Chemistry, Organic

Synthesis of enantiomerically pure fire ant venom alkaloids: Solenopsins and isosolenopsins A, B and C

H. M. T. Bandara Herath et al.

JOURNAL OF HETEROCYCLIC CHEMISTRY (2009)

Article Chemistry, Applied

Anti-cancer effect of two alkaloids: 2R and 2S-bgugaine on mastocytoma P815 and carcinoma Hep

Malika Benamar et al.

NATURAL PRODUCT RESEARCH (2009)

Review Plant Sciences

Alkaloids from amphibian skin: A tabulation of over eight-hundred compounds

JW Daly et al.

JOURNAL OF NATURAL PRODUCTS (2005)

Article Biochemistry & Molecular Biology

Hemlock alkaloids from Socrates to poison aloes

T Reynolds

PHYTOCHEMISTRY (2005)

Review Food Science & Technology

Poison hemlock (Conium maculatum L.)

J Vetter

FOOD AND CHEMICAL TOXICOLOGY (2004)

Article Chemistry, Organic

Enantioselective total synthesis of (+)-azimine and (+)-carpaine

T Sato et al.

ORGANIC LETTERS (2003)

Review Biochemistry & Molecular Biology

Pyrrole, pyrrolidine, pyridine, piperidine and tropane alkaloids

D O'Hagan

NATURAL PRODUCT REPORTS (2000)