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Literature DB >> 21644563

Diversity-oriented synthesis of 2,4,6-trisubstituted piperidines via type II anion relay chemistry.

Abstract

An effective, general protocol for the Diversity-Oriented Synthesis (DOS) of 2,4,6-trisubstituted piperidine congeners has been designed and validated. The successful strategy entails a modular approach to all possible stereoisomers of the selected piperidine scaffold, exploiting Type II Anion Relay Chemistry (ARC), followed in turn by intramolecular S(N)2 cyclization, chemoselective removal of the dithiane moieties and carbonyl reductions.

Entities: Chemical Disease Gene

Mesh：

Substances：
Anions
Ketones
Piperidines

Year: 2011 PMID： 21644563 PMCID： PMC3135908 DOI： 10.1021/ol2010598

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

26 in total

Review 1. Target-oriented and diversity-oriented organic synthesis in drug discovery.

Authors: S L Schreiber
Journal: Science Date: 2000-03-17 Impact factor: 47.728

2. (1S,3R,4R)-2-Azanorbornylmethanol, an Efficient Ligand for Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation of Ketones.

Authors: Diego A. Alonso; David Guijarro; Pedro Pinho; Oliver Temme; Pher G. Andersson
Journal: J Org Chem Date: 1998-04-17 Impact factor: 4.354

3. Deprotecting dithiane-containing alkaloids.

Authors: F F Fleming; L Funk; R Altundas; Y Tu
Journal: J Org Chem Date: 2001-09-21 Impact factor: 4.354

4. The Spongistatins: Architecturally Complex Natural Products-Part One: A Formal Synthesis of (+)-Spongistatin 1 by Construction of an Advanced ABCD Fragment Financial support was provided by the National Institutes of Health (National Cancer Institute) through Grant CA-70329, NIH Postdoctoral Fellowships to A.M.B. and W.H.M., a Japan Society for Promotion of Science Fellowship to N.M., and a Royal Society Fulbright Fellowship to V.A.D. We also thank the Daiichi Pharmaceutical Co., Ltd, and the Tanabe Seiyaku Co., Ltd for financial support. Finally we thank Dr. George T. Furst, Dr. Patrick J. Carroll, Dr. Rakesh Kohli, and Mr John Dykins of the University of Pennsylvania Spectroscopic Service Center for assistance in securing and interpreting high-field NMR spectra, X-ray crystal structures, and mass spectra.

Authors: Amos B. Smith III; Victoria A. Doughty; Qiyan Lin; Linghang Zhuang; Mark D. McBriar; Armen M. Boldi; William H. Moser; Noriaki Murase; Kiyoshi Nakayama; Masao Sobukawa
Journal: Angew Chem Int Ed Engl Date: 2001-01-05 Impact factor: 15.336

5. The first directed reduction of beta-alkoxy ketones to anti-1,3-diol monoethers: identification of spectator and director alkoxy groups.

Authors: G E Keck; C A Wager
Journal: Org Lett Date: 2000-07-27 Impact factor: 6.005

6. Imino Diels-Alder-Based Construction of a Piperidine A-Ring Unit for Total Synthesis of the Marine Hepatotoxin Cylindrospermopsin.

Authors: Geoffrey R. Heintzelman; Steven M. Weinreb; Masood Parvez
Journal: J Org Chem Date: 1996-07-12 Impact factor: 4.354

7. Anion Relay Chemistry: Development of an Effective Diastereoselective [3+2] Annulation Tactic Exploiting an Aldol/Brook Rearrangement/Cyclization Cascade.

Authors: Heeoon Han; Amos B Smith
Journal: Angew Chem Int Ed Engl Date: 2017-10-10 Impact factor: 15.336

8. Total Synthesis of (-)-Secu'amamine A Exploiting Type II Anion Relay Chemistry.

Authors: Heeoon Han; Amos B Smith
Journal: Org Lett Date: 2015-08-20 Impact factor: 6.005

8 in total

Diversity-oriented synthesis of 2,4,6-trisubstituted piperidines via type II anion relay chemistry.

Review 1. Target-oriented and diversity-oriented organic synthesis in drug discovery.

2. (1S,3R,4R)-2-Azanorbornylmethanol, an Efficient Ligand for Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation of Ketones.

3. Deprotecting dithiane-containing alkaloids.

5. The first directed reduction of beta-alkoxy ketones to anti-1,3-diol monoethers: identification of spectator and director alkoxy groups.

6. Imino Diels-Alder-Based Construction of a Piperidine A-Ring Unit for Total Synthesis of the Marine Hepatotoxin Cylindrospermopsin.

7. The effect of HMPA on the reactivity of epoxides, aziridines, and alkyl halides with organolithium reagents.

Review 8. Polyketide biosynthesis beyond the type I, II and III polyketide synthase paradigms.

9. (+)-Rimocidin synthetic studies. Construction of an advanced C(1-18) polyol fragment.

10. Synthesis of bridged azabicyclic structures via ring-closing olefin metathesis.

1. Synthesis of cyclic 1,3-diols as scaffolds for spatially directed libraries.

2. Stereoselective Tandem Bis-Electrophile Couplings of Diborylmethane.

3. Reversed-Polarity Synthesis of Diaryl Ketones through Palladium-Catalyzed Direct Arylation of 2-Aryl-1,3-dithianes.

4. A unified synthetic strategy to the Cryptocarya family of natural products exploiting Anion Relay Chemistry (ARC).

5. Long-range anion relay chemistry (LR-ARC): a validated ARC tactic.

6. Synthetic Access to the Mandelalide Family of Macrolides: Development of an Anion Relay Chemistry Strategy.

7. Anion Relay Chemistry: Development of an Effective Diastereoselective [3+2] Annulation Tactic Exploiting an Aldol/Brook Rearrangement/Cyclization Cascade.

8. Total Synthesis of (-)-Secu'amamine A Exploiting Type II Anion Relay Chemistry.