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Literature DB >> 12201723

Total synthesis of luminacin D.

J Brad Shotwell¹, Evan S Krygowski, John Hines, Brian Koh, Elliott W D Huntsman, Hui Won Choi, John S Schneekloth, John L Wood, Craig M Crews.

Abstract

[reaction: see text] A highly convergent synthesis of the angiogenesis inhibitor luminacin D has been achieved in 13 linear steps (19 steps total, 5.3% overall yield) utilizing a samarium(II) iodide-mediated mixed tandem aldol/Evans-Tishchenko reaction to construct the carbohydrate precursor. The modular synthetic design will allow derivatization at key positions necessary for biochemical mode of action studies.

Entities: Chemical

Mesh：

Substances：

Year: 2002 PMID： 12201723 PMCID： PMC2556570 DOI： 10.1021/ol026382q

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

12 in total

1. First Catalytic Asymmetric Aldol-Tishchenko Reaction-Insight into the Catalyst Structure and Reaction Mechanism J.P.M. gratefully acknowledges receipt of an NSF Career Award (CHE-9875488), a David and Lucile Packard Fellowship and a DuPont Young Professor Grant. Support from Amoco Chemicals is also appreciated. The authors thank Prof. Joseph Templeton for helpful discussions and Andrew Larsen of the Gagné research group for assistance with vapor pressure osmometry experiments.

Authors: Cheryl M. Mascarenhas; Steven P. Miller; Peter S. White; James P. Morken
Journal: Angew Chem Int Ed Engl Date: 2001-02-02 Impact factor: 15.336

2. Luminacins: a family of capillary tube formation inhibitors from Streptomyces sp. I. Taxomony, fermentation, isolation, physico-chemical properties and structure elucidation.

Authors: N Naruse; R Kageyama-Kawase; Y Funahashi; T Wakabayashi
Journal: J Antibiot (Tokyo) Date: 2000-06 Impact factor: 2.649

3. Effect of Calcium Reagents on Aldol Reactions of Phenolic Enolates with Aldehydes in Alcohol.

Authors: Hiroyuki Saimoto; Koji Yoshida; Tetsuya Murakami; Minoru Morimoto; Hitoshi Sashiwa; Yoshihiro Shigemasa
Journal: J Org Chem Date: 1996-10-04 Impact factor: 4.354

Review 4. Tumor angiogenesis: past, present and the near future.

Authors: R S Kerbel
Journal: Carcinogenesis Date: 2000-03 Impact factor: 4.944

5. Stereoselective synthesis of delta-lactones from 5-oxoalkanals via one-pot sequential acetalization, Tishchenko reaction, and lactonization by cooperative catalysis of samarium Ion and mercaptan.

Authors: J L Hsu; J M Fang
Journal: J Org Chem Date: 2001-12-14 Impact factor: 4.354

6. UCS15A, a non-kinase inhibitor of Src signal transduction.

Authors: S V Sharma; C Oneyama; Y Yamashita; H Nakano; K Sugawara; M Hamada; N Kosaka; T Tamaoki
Journal: Oncogene Date: 2001-04-19 Impact factor: 9.867

7. Characterization of rat aortic fragment within collagen gel as an angiogenesis model; capillary morphology may reflect the action mechanisms of angiogenesis inhibitors.

Authors: Naoko Hata-Sugi; Rena Kawase-Kageyama; Toshiaki Wakabayashi
Journal: Biol Pharm Bull Date: 2002-04 Impact factor: 2.233

Total synthesis of luminacin D.

2. Luminacins: a family of capillary tube formation inhibitors from Streptomyces sp. I. Taxomony, fermentation, isolation, physico-chemical properties and structure elucidation.

3. Effect of Calcium Reagents on Aldol Reactions of Phenolic Enolates with Aldehydes in Alcohol.

Review 4. Tumor angiogenesis: past, present and the near future.

5. Stereoselective synthesis of delta-lactones from 5-oxoalkanals via one-pot sequential acetalization, Tishchenko reaction, and lactonization by cooperative catalysis of samarium Ion and mercaptan.

6. UCS15A, a non-kinase inhibitor of Src signal transduction.

7. Characterization of rat aortic fragment within collagen gel as an angiogenesis model; capillary morphology may reflect the action mechanisms of angiogenesis inhibitors.

8. Samarium Ion-Promoted Cross-Aldol Reactions and Tandem Aldol/Evans-Tishchenko Reactions.

9. Luminacins: a family of capillary tube formation inhibitors from Streptomyces sp. II. Biological activities.

10. The promise of anti-angiogenic cancer therapy.

1. Enantioselective Evans-Tishchenko reduction of β-hydroxyketone catalyzed by lithium binaphtholate.