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Literature DB >> 20704319

Total syntheses of arylindolizidine alkaloids (+)-ipalbidine and (+)-antofine.

Abstract

This paper presents the first application of two recently developed reactions to natural product synthesis. The first method involves a 6-endo-trig cyclization to prepare a versatile chiral enaminone building block. The second is a direct C-H arylation reaction. As a showcase for the utility of these methods, (+)-antofine and (+)-ipalbidine were synthesized in only 8 steps and 24-26% overall yields.

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Year: 2010 PMID： 20704319 PMCID： PMC2948484 DOI： 10.1021/jo101051w

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

23 in total

1. New Synthetic Route to 2-Pyridones and Its Application toward the Synthesis of (+/-)-Ipalbidine.

Authors: Scott M. Sheehan; Albert Padwa
Journal: J Org Chem Date: 1997-02-07 Impact factor: 4.354

2. The interaction between tylophorine B and TMV RNA.

Authors: Zhen Xi; Ruoyu Zhang; Zhihong Yu; Di Ouyang
Journal: Bioorg Med Chem Lett Date: 2006-06-12 Impact factor: 2.823

3. Expedient syntheses of antofine and cryptopleurine via intramolecular 1,3-dipolar cycloaddition.

Authors: Sanghee Kim; Yun Mi Lee; Jaekwang Lee; Taeho Lee; Ye Fu; Yanling Song; Jihee Cho; Deukjoon Kim
Journal: J Org Chem Date: 2007-05-25 Impact factor: 4.354

4. Amino acid-derived enaminones: a study in ring formation providing valuable asymmetric synthons.

Authors: Brandon J Turunen; Gunda I Georg
Journal: J Am Chem Soc Date: 2006-07-12 Impact factor: 15.419

5. [Effect of norepinephrinergic system on ipalbidine analgesia].

Authors: L M Wang; Y H Chu
Journal: Yao Xue Xue Bao Date: 1996

6. Synthesis and structure-activity studies of antofine analogues as potential anticancer agents.

Authors: Ye Fu; Sang Kook Lee; Hye-Young Min; Taeho Lee; Jaekwang Lee; Maosheng Cheng; Sanghee Kim
Journal: Bioorg Med Chem Lett Date: 2006-09-30 Impact factor: 2.823

7. Total syntheses of the tylophora alkaloids cryptopleurine, (-)-antofine, (-)-tylophorine, and (-)-ficuseptine C.

Authors: Alois Fürstner; Jason W J Kennedy
Journal: Chemistry Date: 2006-09-25 Impact factor: 5.236

8. Selective interaction between tylophorine B and bulged DNA.

Authors: Zhen Xi; Ruoyu Zhang; Zhihong Yu; Di Ouyang; Runqiu Huang
Journal: Bioorg Med Chem Lett Date: 2005-05-16 Impact factor: 2.823

9. Antitumor agents. 274. A new synthetic strategy for E-ring SAR study of antofine and cryptopleurine analogues.

Authors: Xiaoming Yang; Qian Shi; Kenneth F Bastow; Kuo-Hsiung Lee
Journal: Org Lett Date: 2010-04-02 Impact factor: 6.005

Review 10. Indolizidine and quinolizidine alkaloids.

Authors: Joseph P Michael
Journal: Nat Prod Rep Date: 2007-12-13 Impact factor: 13.423

12 in total

1. Enantiospecific Synthesis and Biological Investigations of a Nuphar Alkaloid: Proposed Structure of a Castoreum Component.

Authors: Hajime Seki; Gunda I Georg
Journal: European J Org Chem Date: 2014-06-01

9. Biomimetic Aerobic C-H Olefination of Cyclic Enaminones at Room Temperature: Development toward the Synthesis of 1,3,5-Trisubstituted Benzenes.

Authors: Yi-Yun Yu; Gunda I Georg
Journal: Adv Synth Catal Date: 2014-04-14 Impact factor: 5.837

10. Boron-Heck reaction of cyclic enaminones: regioselective direct arylation via oxidative palladium(II) catalysis.

Authors: Yong Wook Kim; Gunda I Georg
Journal: Org Lett Date: 2014-03-03 Impact factor: 6.005

Total syntheses of arylindolizidine alkaloids (+)-ipalbidine and (+)-antofine.

1. New Synthetic Route to 2-Pyridones and Its Application toward the Synthesis of (+/-)-Ipalbidine.

2. The interaction between tylophorine B and TMV RNA.

3. Expedient syntheses of antofine and cryptopleurine via intramolecular 1,3-dipolar cycloaddition.

4. Amino acid-derived enaminones: a study in ring formation providing valuable asymmetric synthons.

5. [Effect of norepinephrinergic system on ipalbidine analgesia].

6. Synthesis and structure-activity studies of antofine analogues as potential anticancer agents.

7. Total syntheses of the tylophora alkaloids cryptopleurine, (-)-antofine, (-)-tylophorine, and (-)-ficuseptine C.

8. Selective interaction between tylophorine B and bulged DNA.

9. Antitumor agents. 274. A new synthetic strategy for E-ring SAR study of antofine and cryptopleurine analogues.

Review 10. Indolizidine and quinolizidine alkaloids.

1. Enantiospecific Synthesis and Biological Investigations of a Nuphar Alkaloid: Proposed Structure of a Castoreum Component.

2. Direct Hiyama cross-coupling of enaminones with triethoxy(aryl)silanes and dimethylphenylsilanol.

3. Total synthesis of (+)-antofine and (-)-cryptopleurine.

4. Three-component synthesis of cyclic enaminones via ketene cyclization.

5. Total Syntheses and Cytotoxicity of (R)- and (S)-Boehmeriasin A.

6. Synthesis of amino acid derived enaminones via Wolff rearrangement using vinylogous amides as carbon nucleophiles.

7. Palladium-catalyzed direct C-H arylation of cyclic enaminones with aryl iodides.

8. Copper-assisted palladium(II)-catalyzed direct arylation of cyclic enaminones with arylboronic acids.

9. Biomimetic Aerobic C-H Olefination of Cyclic Enaminones at Room Temperature: Development toward the Synthesis of 1,3,5-Trisubstituted Benzenes.

10. Boron-Heck reaction of cyclic enaminones: regioselective direct arylation via oxidative palladium(II) catalysis.