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Literature DB >> 16706524

A concise stereoselective synthesis of Preussin, 3-epi-Preussin, and analogues.

Abstract

[reaction: see text] A new stereoselective synthesis of the antifungal and antitumor agents Preussin and 3-epi-Preussin via a Pd-catalyzed carboamination of a protected amino alcohol is described. The key transformation leads to simultaneous formation of the N-C2 bond and the C1'-aryl bond, and allows installation of the aryl group one step from the end of the sequence. This strategy permits the facile construction of a variety of preussin analogues bearing different aromatic groups.

Entities: Chemical

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Year: 2006 PMID： 16706524 PMCID： PMC2613785 DOI： 10.1021/ol0606435

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

12 in total

1. Short-step syntheses of all stereoisomers of preussin and their bioactivities.

Authors: Masayuki Okue; Hidenori Watanabe; Koji Kasahara; Minoru Yoshida; Sueharu Horinouchi; Takeshi Kitahara
Journal: Biosci Biotechnol Biochem Date: 2002-05 Impact factor: 2.043

2. Inhibition of cyclin-dependent kinase activity and induction of apoptosis by preussin in human tumor cells.

Authors: T V Achenbach; E P Slater; H Brummerhop; T Bach; R Müller
Journal: Antimicrob Agents Chemother Date: 2000-10 Impact factor: 5.191

3. Identification of preussin as a selective inhibitor for cell growth of the fission yeast ts mutants defective in Cdc2-regulatory genes.

Authors: K Kasahara; M Yoshida; J Eishima; K Takesako; T Beppu; S Horinouchi
Journal: J Antibiot (Tokyo) Date: 1997-03 Impact factor: 2.649

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Authors: J H Johnson; D W Phillipson; A D Kahle
Journal: J Antibiot (Tokyo) Date: 1989-07 Impact factor: 2.649

5. L-657,398, a novel antifungal agent: fermentation, isolation, structural elucidation and biological properties.

Authors: R E Schwartz; J Liesch; O Hensens; L Zitano; S Honeycutt; G Garrity; R A Fromtling; J Onishi; R Monaghan
Journal: J Antibiot (Tokyo) Date: 1988-12 Impact factor: 2.649

6. Palladium-catalyzed tandem N-arylation/carboamination reactions for the stereoselective synthesis of N-aryl-2-benzyl pyrrolidines.

Authors: Qifei Yang; Joshua E Ney; John P Wolfe
Journal: Org Lett Date: 2005-06-23 Impact factor: 6.005

7. Selective synthesis of 5- or 6-aryl octahydrocyclopenta[b]pyrroles from a common precursor through control of competing pathways in a Pd-catalyzed reaction.

Authors: Joshua E Ney; John P Wolfe
Journal: J Am Chem Soc Date: 2005-06-22 Impact factor: 15.419

8. Structure-activity relationships of synthetic antibiotic analogues of anisomycin.

Authors: S S Hall; D Loebenberg; D P Schumacher
Journal: J Med Chem Date: 1983-04 Impact factor: 7.446

9. Palladium-catalyzed synthesis of N-aryl pyrrolidines from gamma-(N-Arylamino) alkenes: evidence for chemoselective alkene insertion into Pd--N bonds.

Authors: Joshua E Ney; John P Wolfe
Journal: Angew Chem Int Ed Engl Date: 2004-07-05 Impact factor: 15.336

10. A flexible approach to (S)-5-alkyl tetramic acid derivatives: application to the asymmetric synthesis of (+)-preussin and protected (3S,4S)-AHPPA.

Authors: Pei-Qiang Huang; Tian-Jun Wu; Yuan-Ping Ruan
Journal: Org Lett Date: 2003-11-13 Impact factor: 6.005

15 in total

1. Use of aryl chlorides as electrophiles in Pd-catalyzed alkene difunctionalization reactions.

Authors: Brandon R Rosen; Joshua E Ney; John P Wolfe
Journal: J Org Chem Date: 2010-04-16 Impact factor: 4.354

2. Palladium-catalyzed alkene carboamination reactions for the synthesis of substituted piperazines.

Authors: Josephine S Nakhla; Danielle M Schultz; John P Wolfe
Journal: Tetrahedron Date: 2009-09-15 Impact factor: 2.457

3. Two palladium-catalyzed domino reactions from one set of substrates/reagents: efficient synthesis of substituted indenes and cis-stilbenoid hydrocarbons from the same internal alkynes and hindered Grignard reagents.

Authors: Cheng-Guo Dong; Pik Yeung; Qiao-Sheng Hu
Journal: Org Lett Date: 2007-01-18 Impact factor: 6.005

4. Palladium-Catalyzed Carboetherification and Carboamination Reactions of γ-Hydroxy- and γ-Aminoalkenes for the Synthesis of Tetrahydrofurans and Pyrrolidines.

Authors: John P Wolfe
Journal: European J Org Chem Date: 2007-02

5. Mild conditions for the synthesis of functionalized pyrrolidines via Pd-catalyzed carboamination reactions.

Authors: Myra Beaudoin Bertrand; Matthew L Leathen; John P Wolfe
Journal: Org Lett Date: 2007-02-01 Impact factor: 6.005

6. Influence of hydroxylamine conformation on stereocontrol in Pd-catalyzed isoxazolidine-forming reactions.

Authors: Georgia S Lemen; Natalie C Giampietro; Michael B Hay; John P Wolfe
Journal: J Org Chem Date: 2009-03-20 Impact factor: 4.354

7. Stereoselective Synthesis of Saturated Heterocycles via Pd-Catalyzed Alkene Carboetherification and Carboamination Reactions.

Authors: John P Wolfe
Journal: Synlett Date: 2006-11-13 Impact factor: 2.454

8. A concise asymmetric synthesis of cis-2,6-disubstituted N-aryl piperazines via Pd-catalyzed carboamination reactions.

Authors: Josephine S Nakhla; John P Wolfe
Journal: Org Lett Date: 2007-07-25 Impact factor: 6.005

9. Mild conditions for Pd-catalyzed carboamination of N-protected hex-4-enylamines and 1-, 3-, and 4-substituted pent-4-enylamines. Scope, limitations, and mechanism of pyrrolidine formation.

Authors: Myra Beaudoin Bertrand; Joshua D Neukom; John P Wolfe
Journal: J Org Chem Date: 2008-10-23 Impact factor: 4.354

10. Stereoselective synthesis of imidazolidin-2-ones via Pd-catalyzed alkene carboamination. Scope and limitations.

Authors: Jonathan A Fritz; John P Wolfe
Journal: Tetrahedron Date: 2008 Impact factor: 2.457